Sythesis and the reagents

50
ISSN 0265-4245 56082–56303 January 2005 Graphical abstracts of new developments www.rsc.org/mos METHODS IN ORGANIC SYNTHESIS CONTENTS Editorial . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Angewandte Chemie, International Edition . . . . . . . . . . . . . . . . . 3 Chemical Communications . . . . . . . . . . . . . . . . . . . . . . . . 4 European Journal of Organic Chemistry . . . . . . . . . . . . . . . . . . 8 Helvetica Chimica Acta . . . . . . . . . . . . . . . . . . . . . . . . . . 8 Journal of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . . 8 Journal of the American Chemical Society . . . . . . . . . . . . . . . . 10 New Journal of Chemistry . . . . . . . . . . . . . . . . . . . . . . . 15 Organic & Biomolecular Chemistry . . . . . . . . . . . . . . . . . . . . 15 Organic Letters . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15 Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23 Synthetic Communications . . . . . . . . . . . . . . . . . . . . . . . 27 Tetrahedron . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33 Tetrahedron Letters . . . . . . . . . . . . . . . . . . . . . . . . . . 35 Books, Reviews and Conference Proceedings . . . . . . . . . . . . . . . 40 Author Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41 Reagent Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43 Reaction Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45 Reactant Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46 Product Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47 Journal Selection . . . . . . . . . . . . . . . . . . . . . . . . . . . 49 Abbreviations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50 © Royal Society of Chemistry 2005

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Transcript of Sythesis and the reagents

  • ISSN 0265-4245 5608256303 January 2005

    Graphical abstracts ofnew developments

    www.rsc.org/mos

    METHODS INORGANIC SYNTHESIS

    CONTENTS

    Editorial . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

    Angewandte Chemie, International Edition . . . . . . . . . . . . . . . . . 3Chemical Communications . . . . . . . . . . . . . . . . . . . . . . . . 4European Journal of Organic Chemistry . . . . . . . . . . . . . . . . . . 8Helvetica Chimica Acta . . . . . . . . . . . . . . . . . . . . . . . . . . 8Journal of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . . 8Journal of the American Chemical Society . . . . . . . . . . . . . . . . 10New Journal of Chemistry . . . . . . . . . . . . . . . . . . . . . . . 15Organic & Biomolecular Chemistry . . . . . . . . . . . . . . . . . . . . 15Organic Letters . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23Synthetic Communications . . . . . . . . . . . . . . . . . . . . . . . 27Tetrahedron . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33Tetrahedron Letters . . . . . . . . . . . . . . . . . . . . . . . . . . 35

    Books, Reviews and Conference Proceedings . . . . . . . . . . . . . . . 40

    Author Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 41Reagent Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 43Reaction Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 45Reactant Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . 46Product Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 47

    Journal Selection . . . . . . . . . . . . . . . . . . . . . . . . . . . 49Abbreviations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 50

    Royal Society of Chemistry 2005

  • Editorial

    2 METHODS IN ORGANIC SYNTHESIS January 2005

    Editorial

    Structure-searchable access to Methods in Organic Synthesis

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    database has been designed with the synthetic organic chemist in mind. It contains data from Methods in Organic Synthesis from 1991 onwards. There are currently over 40,000 reactions and this is growing at the rate of approximately 3,500 new reactions each year. The MOS database has been designed for use with the popular Accord and ISIS reaction-retrieval systems on both desktop and client/server platforms. It is compatible with reaction databases supplied by Accelrys and other reputable database vendors, as well as with in-house systems built using the same database systems.

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    Dr Graham McCann CSci CChem MRSC Managing Editor, Methods in Organic Synthesis www.rsc.org/mos [email protected]

  • Angewandte Chemie, International Edition

    Angewandte Chemie, International Edition

    56082 A practical and mild method for the highly selective conversion of terminal alkenes into aldehydesthrough epoxidationisomerization with ruthenium(IV)catalystsJ. Chen, C.-M. Che*, Angew. Chem., Int. Ed., 2004, 43(37), 4950-4954

    catalyst

    CDCl3, 60 C, 2 h14 examples (8199%) 96%

    CHO2,6-dichloropyridine N-oxide,

    air

    RuCl

    Cl

    catalyst =

    56083 Enantioselective hydrogenation of -ketoesters with monodentate ligandsK. Junge, B. Hagemann, S. Enthaler, G. Oehme, M. Michalik, X. Monsees, T. Riermeier, U. Dingerdissen, M. Beller*, Angew.Chem., Int. Ed., 2004, 43(38), 5066-5069

    80 C, H2 (60 bar), 16 h

    >99%, 28% ee (S)38 examples (28>99%, 295% ee)

    [L2RuBr2]H3C OCH3

    O O

    H3C OCH3

    OH O

    OO

    P OPhL =

    56084 Difluoromethyl phenyl sulfone, a difluoromethylidene equivalent: use in the synthesis of1,1-difluoro-1-alkenesG. K. S. Prakash*, J. Hu, Y. Wang, G. A. Olah, Angew. Chem., Int. Ed., 2004, 43(39), 5203-5206

    The alkyl-substituted difluoromethyl sulfones can be synthesized from difluoromethyl phenyl sulfone, theappropriate alkyl iodide and potassium tert-butoxide (13 examples, 3784%)

    THF, 20 C rt

    87%8 examples (5588%)

    tBuOKPhO SO2Ph PhO

    56085 Evidence for the formation of an iodosylbenzene(salen)iron(III)-catalyzed asymmetric sulfide oxidationK. P. Bryliakov*, E. P. Talsi, Angew. Chem., Int. Ed., 2004, 43(39), 5228-5230

    CH2Cl2, 0 C, 2 h

    94% conversion,92% selectivity,

    58% ee (S)-()-isomer3 examples (7466% conversion,

    catalystPh S

    PhPh S

    Ph

    O

    6999% selectivity,2062% ee)

    N N

    O OFe

    Cl

    H H

    catalyst =

    PhIO

    56086 Development of a ruthenium-catalyzed asymmetric epoxidation procedure with hydrogen peroxide asthe oxidantM. K. Tse, C. Dobler, S. Bhor, M. Klawonn, W. Magerlein, H. Hugl, M. Beller*, Angew. Chem., Int. Ed., 2004, 43(39), 5255-5260

    tBuOH, rt, 12 h

    12 examples (59100% yield, 72100% selectivity, 2884% ee)

    30% aq. H2O2Ph Ph

    Ocatalyst

    93% yield93% selectivity

    80% ee

    catalyst =

    NO

    N N

    O

    Ru

    NO

    O

    O

    O

    METHODS IN ORGANIC SYNTHESIS January 2005 3

  • Angewandte Chemie, International Edition

    56087 Gold(I)-catalyzed 5-endo-dig carbocyclization of acetylenic dicarbonyl compoundsS. T. Staben, J. J. Kennedy-Smith, F. D. Toste*, Angew. Chem., Int. Ed., 2004, 43(40), 5350-5352

    CH2Cl2, rt, 5 min

    83%12 examples (7499%)

    [Au(PPh3)]Cl, AgOTfOMe

    O O

    MeO

    O

    O

    56088 Ru- and Rh-catalyzed CC bond cleavage of cyclobutanones: reconstructive and selective synthesis of2-pyranones, cyclopentenes, and cyclohexenonesT. Kondo, Y. Taguchi, Y. Kaneko, M. Niimi, T. Mitsudo*, Angew. Chem., Int. Ed., 2004, 43(40), 5369-5372

    toluene, 100 C, 2 h

    86%4 examples (7586%)

    [RhCl(CO)2]2 or [RuCl2(CO)3]2O O

    O

    56089 Carboamination: additions of imine C1N bonds across alkynes catalyzed by imidozirconium complexesR. T. Ruck, R. L. Zuckermann, S. W. Krska, R. G. Bergmann*, Angew. Chem., Int. Ed., 2004, 43(40), 5372-5374

    C6D6, 145 C, 3096 h80%7 examples (5885%)

    NNCp2Zr N

    Ph Ph

    OMe

    O

    Ph

    O

    Ph

    PhPh

    56090 Zirconium-mediated conversion of amides to nitriles: a surprising additive effectR. T. Ruck, R. G. Bergmann*, Angew. Chem., Int. Ed., 2004, 43(40), 5375-5377

    [D8]THF, 105 C, 48 h8 examples (91100%)

    Cp2ZrMe2NH2

    O

    96%

    LiClCN

    56091 Electrophilic alkylations in neutral aqueous or alcoholic solutionsM. Hoffmann, N. Hampel, T. Kanzian, H. Mayr*, Angew. Chem., Int. Ed., 2004, 43(40), 5402-5405

    CF3CH2OH, rt

    70%19 examples (33100%)

    2,6-lutidineCl

    MeO MeO

    OO

    Chemical Communications

    56092 Direct arylation of aromatic CH bonds catalyzed by Cp*Ir complexesK.-i. Fujita*, M. Nonogawa, R. Yamaguchi*, Chem. Commun., 2004, (17), 1926-1927

    [5-C5Me5IrHCl]2KOtBu, 80 C, 30 h

    9 examples (3272%) 70%

    I

    4 METHODS IN ORGANIC SYNTHESIS January 2005

  • Chemical Communications

    56093 First catalytic asymmetric synthesis of -amino--polyfluoroalkyl ketones via proline-catalysed directasymmetric carboncarbon bond formation reaction of polyfluoroalkylated aldiminesK. Funabiki*, M. Nagamori, S. Goushi, M. Matsui, Chem. Commun., 2004, (17), 1928-1929

    L-prolineacetone, rt, 7 d

    19 examples (ee 20.498.0%) 98% ee, 71% yield, 99 : 1 = S : RC6H4OMe-p

    O

    F2HC

    NH Op-MeOC6H4F

    F

    56094 A highly efficient gold/silver-catalyzed addition of arenes to iminesY. Luo, C.-J. Li*, Chem. Commun., 2004, (17), 1930-1931

    CH2Cl2, 0 C, 12 h

    9 examples (3485%) 85%

    AuCl3AgOTf

    OMe

    MeO OMeEtO2CHC NTs

    OMe

    MeO OMe

    CO2Et

    NHTs

    56095 CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium andphosphineD. Ma*, F. Liu, Chem. Commun., 2004, (17), 1934-1935

    CuIN,N-dimethylglycineK2CO3, DMF, 100 C, 24 h

    26 examples (6098%) 98%

    H3-NO2C6H4I 3-NO2C6H4Ph Ph

    56096 Radical addition of nitrones to acrylates mediated by SmI2: asymmetric synthesis of -amino acidsemploying carbohydrate-based chiral auxiliariesS. A. Johannesen, S. Albu, R. G. Hazell, T. Skrydstrup*, Chem. Commun., 2004, (17), 1962-1963

    THF, 78 C, 20 h

    9 examples (5480%) 71%, >95 : 5 ds

    SmI2O

    Cy

    N O

    OO

    O

    OnBuO

    Cy

    N HO

    OO

    O

    OnBu

    56097 (Bu3Sn)2TBAF: a new combination reagent for the reduction and deuteration of aryl bromides and iodidesD. C. Harrowven*, I. L. Guy, M. I. T. Nunn, Chem. Commun., 2004, (17), 1966-1967

    (Bu3Sn)2TBAFPhMe, 90 C, 1 h

    13 examples (9099%) 97%

    O

    O

    HSS

    Br

    O

    O

    HSS

    56098 Palladium catalysed cross-coupling reactions of silylaminesC. J. Smith*, T. R. Early, A. B. Holmes*, R. E. Shute, Chem. Commun., 2004, (17), 1976-1977

    Pd(OAc)2,P(t-Bu)2(o-biphen)Sc2Co3, scCO2,

    100 C, 17 h

    18 examples (2584%) 84%

    CO2Me

    NTMS

    CO2Me

    Br

    MeO2C CO2Me

    N

    METHODS IN ORGANIC SYNTHESIS January 2005 5

  • Chemical Communications

    56099 A highly efficient heterogeneous catalytic system for Heck reactions with a palladium colloid layerreduced in situ in the channel of mesoporous silica materialsL. Li, J.-l. Shi*, J.-n. Yan, Chem. Commun., 2004, (17), 1990-1991

    NEt3, 120 C, 50 min

    8 examples (conversion 37100%, yield 8599%) 100% conversion, 99% yield

    Pd-SBABr COMe

    PhMeOC

    Ph

    56100 Highly efficient and recyclable heterogeneous asymmetric transfer hydrogenation of ketones in waterP. N. Liu, J. G. Deng, Y. Q. Tu*, S. H. Wang, Chem. Commun., 2004, (18), 2070-2071

    [RuCl2(p-cymene)]2silica gelBu4NBr, HCO2Na, 311 h

    11 substrate examples (ee 90>99%) >99% conversion, 94% eeCl

    O

    Cl

    OH

    56101 First example of ring expansion of activated quinolines and isoquinolines: novel benzoazepinesJ. S. Yadav*, B. V. Subba Reddy, M. K. Gupta, A. Prabhakar, B. Jagadeesh, Chem. Commun., 2004, (18), 2124-2125

    1,2-dichloroethane,reflux, 0.5 h

    11 examples (8098%) 98%

    Cu(OTf)2N O

    O

    Cl

    N2 CHCOPh N

    COPh

    O

    O

    56102 Practical highly enantioselective synthesis of terminal propargylamines. An expeditious synthesisof (S)-(+)-coniineN. Gommermann, P. Knochel*, Chem. Commun., 2004, (20), 2324-2325

    (i) CuBr, (R)-Quinaptoluene, rt, 3 d

    (ii) TBAF

    15 examples (7297% yield, 8498% ee) 84% yield, 98% ee

    i-PrH

    NBn2

    i-PrCHO H SiMe3 HNBn2

    (R)-Quinap =

    N

    PPh2

    56103 First asymmetric SmI2-induced cross-coupling of Cr(CO)3 aromatic nitrone complexes with carbonylcompoundsM. Chavarot, M. Rivard, F. Rose-Munch*, E. Rose, S. Py, Chem. Commun., 2004, (20), 2330-2331

    THF, 78 C, 30 min

    6 examples (yield 6596%, dr >95 : 5) 96% yield, >95 : 5 dr

    SmI2

    Me

    Cr(CO)3

    NH

    BnO

    But H

    O

    Me

    Cr(CO)3

    NOH

    Bn tBu

    OHH

    56104 An active ferrocenyl triarylphosphine for palladium-catalyzed SuzukiMiyaura cross-coupling of arylhalidesF. Y. Kwong*, K. S. Chan, C. H. Yeung, A. S. C. Chan*, Chem. Commun., 2004, (20), 2336-2337

    Pd2(dba)3, LKF, THF, N2, rt, 24 h

    17 examples (8398%) 98%MeO Br

    OMe

    B(OH)2 MeO

    OMeL =

    PPh2

    Fe

    6 METHODS IN ORGANIC SYNTHESIS January 2005

  • Chemical Communications

    56105 A novel strategy for the preparation of arylhydroxylamines: chemoselective reduction of aromatic nitrocompounds using bakers yeastF. Li, J. Cui*, X. Qian*, R. Zhang, Chem. Commun., 2004, (20), 2338-2339

    baker's yeastphosphate buffer, glucose,

    30 C, 1 h

    10 examples (conversion 86100%,c : d = 70 : 30 to >98 : 2)

    conversion 99%

    NO2

    CNCN CN

    CN

    NHOH NH2

    CNCN

    c>98

    d2

    ::

    56106 Polysulfones: solid organic catalysts for the chemoselective cleavage of methyl-substituted allyl ethersunder neutral conditionsD. Markovic, P. Steunenberg, M. Ekstrand, P. Vogel*, Chem. Commun., 2004, (21), 2444-2445

    cyclohexane, 80 C

    85%12 substrates (8596%)

    OHOHO

    OCH2C(Me)=CH2

    OO

    OHOHO

    OH

    OO

    SO2 SO2Na

    n

    56107 BINOL catalyzed enatioselective addition of titanium phenylacetylide to aromatic ketonesP. G. Cozzi*, S. Alesi, Chem. Commun., 2004, (21), 2448-2449

    BuLi, ClTi(OiPr)3, 30 C, 24 h

    70%, 89% ee8 ketone substrates (2898%, 2890% ee)

    (R,R)-BINOLPh

    O

    +HO

    Ph

    56108 L-Proline catalyzed asymmetric transfer aldol reaction between diacetone alcohol and aldehydesS. Chandrasekhar*, C. Narsihmulu, N. R. Reddy, S. S. Sultana, Chem. Commun., 2004, (21), 2450-2451

    DMSO, rt, 4 h

    86%, 71% ee10 substrates (4091%, 4896% ee)

    L-ProlineH

    O

    +

    O2N

    diacetone alcohol

    NO2

    O OH

    56109 The first tandem double palladium-catalyzed aminations: synthesis of dipyrido[1,2-a:3,2-d]imidazole andits benzo- and aza-analoguesK. T. J. Loones, B. U. W. Maes*, R. A. Dommisse, G. L. F. Lemiere, Chem. Commun., 2004, (21), 2466-2467

    CsCO3, toluene, reflux, 17 h

    96%6 substrates (8298%)

    Pd(OAc)2, BINAP or XANTPHOS+

    NN

    I

    Cl NH2 NN

    N

    56110 Aziridine sulfides and disulfides as catalysts for the enantioselective addition of diethylzinc to aldehydesA. L. Braga*, P. Milani, M. W. Paixao, G. Zeni, O. E. D. Rodrigues, E. F. Alves, Chem. Commun., 2004, (21), 2488-2489

    Toluene, rt, 24 h

    82%, 87% ee (S)5 catalysts (4282%, 37>99% ee)

    +H

    O

    Et2Zn

    OHSN

    Ar

    2

    METHODS IN ORGANIC SYNTHESIS January 2005 7

  • Chemical Communications

    56111 Enantioselective synthesis of allenyl carbinols by the CBS reduction in nitroethane: dramatic solventeffect for reactivity and enantioselectivityC.-M. Yu*, C. Kim, J.-H. Kweon, Chem. Commun., 2004, (21), 2494-2495

    Catecholborane, 78 C, 1 h, CH3CH2NO

    93%, 93% ee6 substrates (8695%, 92>99% ee)

    O

    PhH2CH2CMe

    HO

    PhH2CH2CMe

    HN B

    O

    Me

    Ph Ph

    European Journal of Organic Chemistry

    56112 Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynesT. Jin, S. Kamijo, Y. Yamamoto*, Eur. J. Org. Chem., 2004, (18), 3789-3791

    DMFMeOH, 100 C, 12 h

    83%12 alkynes (5595%)

    CuIH + TMSN3

    NN

    NH

    H

    Helvetica Chimica Acta

    56113 Chrial borate esters in asymmetric synthesis Part 2 Asymmetric borane reduction of prochiral ketones inthe presence of a chiral spiroborate esterD. Liu, Z. Shan*, Y. Zhou, Z. Wu, J. Qin, Helv. Chim. Acta, 2004, 87(9), 2310-2317

    THF, 05 C, 2 h98%, 92% ee7 substrates (692% ee)

    O OH

    + BH3THF

    O

    OB

    O O

    HN

    56114 Versatile one-step one-pot direct aldol condensation promoted by MgI2H.-X. Wei*, K. Li, Q. Zhang, R. L. Jasoni, J. Hu, P. W. Pare*, Helv. Chim. Acta, 2004, 87(9), 2354-2358

    CH2Cl2, rt, 30 min

    98%12 examples (6098%)

    O O

    + H

    O OHMgI2, EtN(iPr)2

    Journal of Organic Chemistry

    56115 Highly regio- and stereoselective synthesis of polysubstituted cyclopropane compounds via thePd(0)-catalyzed couplingcyclization reaction of 2-(2,3-allenyl)malonates with organic halidesS. Ma*, N. Jiao, Q. Yang, Z. Zheng, J. Org. Chem., 2004, 69(19), 6463-6477

    n-Bu4NBr, CH3CN, 16 h

    93%, cis:trans 6:9415 examples (4998%)

    Pd(PPh3)4+ PhI

    n-C6H13CO2Me

    CO2Me

    Ph

    MeO2C CO2Me

    C6H13

    Me

    8 METHODS IN ORGANIC SYNTHESIS January 2005

  • Journal of Organic Chemistry

    56116 A facile synthesis of C2,N3-disubstituted-4-quinazoloneS. Xue*, J. McKenna*, W.-C. Shieh, O. Repic, J. Org. Chem., 2004, 69(19), 6474-6477

    CH3CN,70 C

    95%24 examples (8798%)

    PCl3+

    O

    O

    OH

    O

    NH

    OO

    O

    Cl

    NH2

    O

    O

    N

    O

    NO

    O

    Cl

    56117 Formation of a quaternary carbon center throught the Pd(0)/PhCOOH-catalyzed allylation of cyclic -ketoesters and 1,3-diketones with alkynesN. T. Patil, Y. Yamamoto*, J. Org. Chem., 2004, 69(19), 6478-6481

    Toluene

    98%14 examples (5198%)

    Pd(0)/PhCOOH+

    O

    OEt

    OCl

    O OOEt

    Cl

    56118 Unexpected formation of tetrasubstituted 2,3-dihydrofurans from the reactions of -ketopolyfluoroalkanesulfones with aldehydesC. Xing, S. Zhu*, J. Org. Chem., 2004, 69(19), 6486-6488

    Toluene, reflux, 1 hr

    90%23 examples (7295%)

    Piperidine+Cl(F2C)4O2S Ph

    O

    Br

    O

    H

    O Ph

    SO2(CF2)4Cl

    O

    Ph

    Br

    56119 Solvent free amination reactions of aryl bromides at room temperature catalyzed by a (-allyl)palladiumcomplex bearing a diphosphinidenecyclobutene ligandA. S. Gajare, K. Toyota, M. Yoshifuji*, F. Ozawa, J. Org. Chem., 2004, 69(19), 6504-6506

    rt, 12 h

    98%21 examples (6098%)

    tBuOK, [Pd]+Ph Br Ph NH2 Ph

    HN Ph

    Ph

    Ph

    P

    P

    Mes*

    Mes*

    Pd

    + OTf-

    [Pd] =

    56120 Enantioselective cyanation/Brook rearrangement/C-acylation reactions of acylsilanes catalyzed by chiralmetal alkoxidesD. A. Nicewicz, C. M. Yates, J. S. Johnson*, J. Org. Chem., 2004, 69(20), 6548-6555

    toluene, 45 C, 72 h

    catalystcatalyst =

    10 examples (7082% yield, 6182% ee) 81% yield, 78% ee

    SiEt3

    O

    NC OBn

    O

    F

    CO2Bn

    F

    NC OSiEt3

    NNAl

    OO ClClOiPr

    56121 Arylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles. Partnerrole swapping and heterocycle protectionM. Prieto, E. Zurita, E. Rosa, L. Munoz, P. Lloyd-Williams*, E. Giralt*, J. Org. Chem., 2004, 69(20), 6812-6820

    tolueneEtOHH2O, reflux

    Pd(PPh3)4

    34 examples (up to 99%) 85%NH

    BrMeO

    B(OH)2NH

    MeO

    Na2CO3

    METHODS IN ORGANIC SYNTHESIS January 2005 9

  • Journal of Organic Chemistry

    56122 Base-catalyzed endo-mode cyclization of allenes: easy preparation of five- to nine-membered oxacyclesC. Mukai*, M. Ohta, H. Yamashita, S. Kitagaki, J. Org. Chem., 2004, 69(20), 6867-6873

    tBuOH, 30 C

    tBuOK

    7 examples (7198%) 94%HO

    OTBDMS

    OH

    PO

    OEtOEt

    OPOEt

    OEt

    O

    2. PPTS

    1. (EtO)2PCl, Et3N

    56123 Alkyl- or arylthiolation of aryl iodide via cleavage of the SS bond of disulfide compound by nickelcatalyst and zincN. Taniguchi*, J. Org. Chem., 2004, 69(20), 6904-6906

    DMF, 100 C, 48 h

    NiBr2-bpy, Zn

    16 examples (6192%) 76%

    I

    SS

    S

    56124 The first conversion of primary alkyl halides to nitroalkanes under aqueous mediumR. Ballini*, L. Barboni, G. Carlo, J. Org. Chem., 2004, 69(20), 6907-6908

    H2O, rt, 1 hAgNO2

    13 examples (5390%) 83%I NO2

    56125 Reactions on a solid surface. A simple, economical and efficient FriedelCrafts acylation reaction overzinc oxide (ZnO) as a new catalystM. H. Sarvari, H. Sharghi*, J. Org. Chem., 2004, 69(20), 6953-6956

    The ZnO could be reused 3 times with little loss in activity

    no solvent, rt, 10 minZnO

    14 examples (5098%) 94%O

    Cl Ph

    O OPh

    O

    Journal of the American Chemical Society

    56126 Bifunctional nanocrystalline MgO for chiral epoxy ketones via ClaisenSchmidt condensationasymmetricepoxidation reactionsB. Choudary*, M. Kantam, K. Ranganath, K. Mahendar, B. Sreedhar, J. Am. Chem. Soc., 2004, 126(11), 3396-3397

    i) toluene, 100 Cii) TBHP, 25 C

    10 examples(070% yield098% ee)

    70% yield90% ee

    NAP-MgOO

    +

    O

    CH3Ph HPh Ph Ph

    OO

    56127 PtCl2-catalyzed cycloisomerizations of allenynesN. Cadran, K. Cariou, G. Herve, C. Aubert, L. Fensterbank, M. Malcria*, J. Marco-Contelles, J. Am. Chem. Soc., 2004,126(11), 3408-3409

    PhMe, rt, 2448 h

    12 examples(3290% yield)

    75% yield

    (5 mol%) PtCl2

    H

    MeO

    MeOCH3

    CH3H

    HH

    MeO

    MeO

    10 METHODS IN ORGANIC SYNTHESIS January 2005

  • Journal of the American Chemical Society

    56128 Synthesis of medium ring nitrogen heterocycles via a tandem copper-catalyzed CN bondformationring-expansion processA. Klapars, S. Parris, K. Anderson, S. Buchwald*, J. Am. Chem. Soc., 2004, 126(11), 3529-3533

    N,N-dimethylethylenediamine, K2CO3; PhMe, 110 C, 2224 h

    12 examples(098% yield)

    92% yield

    (5 mol%) CuI+

    NH2

    INH

    O

    NH

    HN

    O

    56129 Bronsted acid-promoted cyclizations of siloxyalkynes with arenes and alkynesL. Zhang, S. A. Kozmin*, J. Am. Chem. Soc., 2004, 126(33), 10204-10205

    CH2Cl2, 20 C

    92%11 examples (7699%)

    HNTf2

    OTIPS OTIPS

    56130 Catalytic deallylation of allyl- and diallylmalonatesD. Necas, M. Tursky, M. Kotora*, J. Am. Chem. Soc., 2004, 126(33), 10222-10223

    H+

    99%16 examples (6899%)

    EtAl3, NiBr2(PPh3)2EtOOC PhEtOOC

    EtOOCPh

    EtOOC

    56131 Catalytic cross-coupling of alkylzinc halides with -chloroketonesC. F. Malosh, J. M. Ready*, J. Am. Chem. Soc., 2004, 126(33), 10240-10241

    THFEt2O

    95%22 examples (7096%)

    Cu(acac)2, ZnCl2O

    Cl+ iPrMgCl

    OiPr

    56132 Palladium-catalyzed cyclization/carboalkyation of alkenyl indolesC. Liu, R. A. Widenhoefer*, J. Am. Chem. Soc., 2004, 126(33), 10250-10251

    MeOH, rt, 0.5 h

    83%15 examples (4592%)

    PdCl2(CH3CN)2, CuCl2HN

    HN

    MeO2C

    56133 Ruthenium catalyzed [3 + 2] intramolecular cycloaddition of alk-5-ynylidenecyclopropanes promoted bythe first-generation Grubbs carbene complexF. Lopez, A. Delgado, J. R. Rodriguez, L. Castedo, J. L. Mascarenas*, J. Am. Chem. Soc., 2004, 126(33), 10262-10263

    toluene, 110 C, 45 min

    78%6 examples (5678%)

    EtO2CEtO2C

    EtO2CEtO2C

    PCy3RuPCy3

    Ph

    ClCl

    METHODS IN ORGANIC SYNTHESIS January 2005 11

  • Journal of the American Chemical Society

    56134 Alkylation of alkenes: ethylaluminium sesquichloride-mediated hydro-alkyl additions with alkylchloroformates and di-tert-butylpyrocarbonateU. Biermann, J. O. Metzger*, J. Am. Chem. Soc., 2004, 126(33), 10319-10330

    CH2CL2, 15 C, 1 h

    82%33 examples (3084%)

    Et3Al2Cl3iPr

    O Cl

    O+

    56135 Self-supported heterogenous catalysts for enantioselective hydrogenationX. Wang, K. Ding, J. Am. Chem. Soc., 2004, 126(34), 10524-10525

    toluene, H2, 4 atm, 25 C, 10 h

    4 examples(>99% conversion89.597.3% ee)

    >99% conversion95% ee

    (1 mol%) catalystH OCH3

    NHAc

    O

    HCO2CH3

    NHAc

    catalyst =O

    OP

    [Rh]N O

    OP

    NLinker

    n

    56136 Regio- and chemoselective direct generation of functionalized aromatic aluminium compounds usingaluminium ate baseM. Uchiyama*, H. Naka, Y. Matsumoto, T. Ohwada, J. Am. Chem. Soc., 2004, 126(34), 10526-10527

    ii) I213 examples

    (40100% yield) 99% yield

    i) iBu3Al(TMP)L, THF, 78 Crt, 112 h

    OMe OMeI

    56137 Nickel-catalyzed intermolecular [3 + 2 + 2] cocyclization of ethyl cyclopropylideneacetate and alkynesS. Saito*, M. Masuda, S. Komagawa, J. Am. Chem. Soc., 2004, 126(34), 10540-10541

    toluene, Ar, rt, one night9 examples

    (2589% yield)

    (10 mol%) Ni(cod)2(20 mol%) PPh3

    COOEt

    + Ph H

    COOEt

    Ph

    HPh

    H

    56138 Intramolecular CN bond addition of amides to alkynes using platinum catalystT. Shimada, I. Nakamura, Y. Yomamoto*, J. Am. Chem. Soc., 2004, 126(34), 10546-10547

    anisole, 80100 C, 0.324 h

    14 examples(0>99% yield)

    (5 mol%) PtCl2+

    94% yield

    Ph

    N Me

    O

    MeN

    Me

    PhO

    MeN

    Me

    H

    Me

    56139 Hydroxyapatite-supported palladium nanoclusters: a highly active heterogenous catalyst for selectiveoxidation of alcohols by use of molecular oxygenK. Mori, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda*, J. Am. Chem. Soc., 2004, 126(34), 10657-10666

    trifluorotoluene, O2 atm, 90 C, 124 h

    Numerous examples(8499% conversion

    8099% yield)

    (0.1 g) PhHAP-0

    97% conversion94% yield

    O

    O

    OH O

    O

    CHO

    12 METHODS IN ORGANIC SYNTHESIS January 2005

  • Journal of the American Chemical Society

    56140 Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents.An effective method for enantioselective synthesis of tertiary and quaternary carbonsM. Kacprzynski, A. Hoveyda*, J. Am. Chem. Soc., 2004, 126(34), 10676-10681

    Et2Zn, THF, 15 C, N2 atm, 24 h

    22 examples(5895% yield7896% ee)

    90% yield91% ee

    (10 mol%) chiral Schiff base(5 mol%) (CuOTf)2C6H6OPO(OEt)2H5C6

    H5C6

    56141 Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenesM. R. Luzung, J. P. Markham, F. D. Toste*, J. Am. Chem. Soc., 2004, 126(35), 10858-10859

    (Ph3P)AuPF6CH2Cl2, rt

    10 examples (6199%) 99%

    Ph

    Ph

    H

    H

    56142 Highly diastereoselective and enantioselective CH functionalization of 1,2-dihydronaphthalenes: acombined CH activation/Cope rearrangement followed by a retro-Cope rearrangementH. M. L. Davies*, Q. Jin, J. Am. Chem. Soc., 2004, 126(35), 10862-10863

    2,2-dimethylbutane, 0 C

    13 examples(yield 5395%, de >98%, ee 9199%) 95% yield, >98% de, 99.5% ee

    Rh2(S-DOSP)4N2

    Ph

    CO2Me

    Ph

    HCO2Me

    Rh2(S-DOSP)4 =

    NSO2Ar

    O

    O

    Rh

    Rh

    H

    4

    56143 Bidentate NHC-based chiral ligands for efficient Cu-catalyzed enantioselective allylic alkylations:structure and activity of an air-stable chiral Cu complexA. O. Larsen, W. Leu, C. N. Oberhuber, J. E. Campbell, A. H. Hoveyda*, J. Am. Chem. Soc., 2004, 126(36), 11130-11131

    N

    Me2Zn, TFH, 15 C, 24 h

    >98% conversion, 74% ee15 examples

    (4294% yield, 7198% ee)

    [Ag], (CuOTf)2.C6H6Ph OPO(OEt)2

    H

    Ph

    HMe

    OAg

    N

    AgO

    NN

    [Ag] =

    56144 Chemoslective silylzincation of functionalized terminal alkynes using dianion-type zincate(SiBNOL-Zn-ate): regiocontrolled synthesis of vinylsilanesS. Nakamura, M. Uchiyama*, T. Ohwada, J. Am. Chem. Soc., 2004, 126(36), 11146-11147

    THF, rt, 12 h

    100%16 examples (73100%)

    [Zn][Zn] =H

    PhH

    HSi

    Ph

    MeMe

    Me OO

    ZnSi

    tBu

    MeMe

    Me

    56145 Catalytic enantioselective Michael addition of 1,3-dicarbonyl compounds to nitroalkenes catalyzed bywell-defined chiral Ru amido complexesM. Watanabe, A. Ikagawa, H. Wang, K. Murata, T. Ikariya*, J. Am. Chem. Soc., 2004, 126(36), 11148-11489

    Toluene, 20 C, 48 h

    99%, 95% ee18 examples (599%, 3098% ee)

    [Ru][Ru] =Ph

    NO2 + CH2(CO2CH3)2Ph

    NO2CH(CO2CH3)2

    NH

    RuNC6H5

    C6H5

    SO O

    METHODS IN ORGANIC SYNTHESIS January 2005 13

  • Journal of the American Chemical Society

    56146 AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-onesT. Yao, X. Zhang, R. C. Larock, J. Am. Chem. Soc., 2004, 126(36), 11164-11165

    CH2Cl2, rt, 1 h

    88%12 examples (5290%)

    AuCl3+ MeOH

    O Ph OPh

    OMe

    56147 Zirconium-catalyzed enantioselective [3+2] cycloaddition of hydrazones to olefins leading to opticallyactive pyrazolidine, pyrazoline and 1,3-diamine derivativesY. Yamashita, S. Kobayashi*, J. Am. Chem. Soc., 2004, 126(36), 11279-11282

    Toluene, 0 C, 18 h

    94%22 examples (6795%, 4298% ee)

    Zr(OPr)4, [L]+N

    PhH2CH2C H

    NH

    O C6H4(p-NO2)

    OEt HN NC6H4(p-NO2)

    O

    PhH2CH2C OEt

    I I

    II

    OMe[L] =

    56148 Highly enantioselective conjugate addition of nitroalkanes to alkylidenemalonates using efficientphase-transfer catalysis of N-spiro chiral ammonium bromidesT. Ooi, S. Fujioka, K. Maruoka*, J. Am. Chem. Soc., 2004, 126(38), 11790-11791

    Toluene, 0 C

    99%, 98% ee9 examples (9799%, 8899% ee)

    Cs2CO3, [N]Et NO2

    CO2iPr

    CO2iPrF

    CO2iPr

    CO2iPrF

    EtO2NN

    Ar

    ArBr

    F3C CF3

    CF3

    CF3

    Ar =

    +

    [N] =

    56149 Organocatalytic asymmetric aza-FriedelCrafts alkylation of furanD. Uraguchi, K. Sorimachi, M. Terada*, J. Am. Chem. Soc., 2004, 126(38), 11804-11805

    1,2-dichloroethane, 35 C, 24 h95%, 96% ee13 substrates (8496%, 8697% ee) Ar = 3,5-dimesityl phenyl

    +OMeO N

    p-MeO-C6H4H

    BocOMeO

    p-MeO-C6H4

    NHBoc

    Ar

    OO

    Ar

    PO

    OH

    56150 Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienesL. Zhang, S. A. Kozmin*, J. Am. Chem. Soc., 2004, 126(38), 11806-11807

    20 C, CH2Cl2

    99%8 substrates (5099%)

    Ph Me

    OTIPS

    AuCl Ph

    TIPSO

    Me

    14 METHODS IN ORGANIC SYNTHESIS January 2005

  • Organic Letters

    56151 New entries in Lewis acidLewis base bifunctional asymmetric catalyst: catalytic enantioselectiveReissert reaction of pyridine derviativesE. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai*, M. Shibasaki*, J. Am. Chem. Soc., 2004, 126(38), 11808-11809

    CH2Cl2, 60 C, 27 h

    98%, 91% ee7 substrates (8598%, 57>99%)

    Et2AlCl, [L]

    N

    NMe2

    O

    + TMSCN + MeOCOCl

    N

    NMe2

    O

    NC

    OHOH

    S

    S

    O

    Ph

    O

    Ph

    [L] =

    New Journal of Chemistry

    56152 Copper promoted synthesis of diaryl ethersR. Ghosh, A. G. Samuelson*, New J. Chem., 2004, 28(11), 1390-1393

    K3PO4, THF, 18 h

    33 examples (7>99%) >99%

    CuCO3Cu(OH)2H2O

    ONa Br

    CN

    O

    CN

    Organic & Biomolecular Chemistry

    56153 Bromine catalyzed conversion of S-tert-butyl groups into versatile and, for self-assembly processesaccessible, acetyl-protected thiolsA. Blaszczyk, M. Elbing, M. Mayor*, Org. Biomol. Chem., 2004, 2(19), 2722-2724

    AcCl/AcOH, rt

    94%9 substrates (2997%)

    Br2Br S Br S

    O

    56154 The first Cu(I)-mediated nucleophilic trifluoromethylation reactions using (trifluoromethyl)trimethylsilanein ionic liquidsJ. Kim, J. M. Shreeve*, Org. Biomol. Chem., 2004, 2(19), 2728-2734

    [IL], 25 C, 3 h

    88%8 examples (8898%)

    CsF, TMSCF3O

    H

    OH

    HCF3 NOO

    O

    N(SO2CF3)[IL] =

    Organic Letters

    56155 Improved procedure for the oxidative cleavage of olefins by OsO4NaIO4W. Yu, Y. Mei, Y. Kang, Z. Hua, Z. Jin*, Org. Lett., 2004, 6(19), 3217-3219

    Use of 2,6-lutidine dramatically improved the yield of aldehyde (from 2144% for the same 5 examples)

    dioxanewater, 25 C, 20 h

    OsO4, NaIO4, 2,6-lutidine

    5 examples (7199%) 99%

    OO

    OTBS

    OO

    CHO

    OTBS

    METHODS IN ORGANIC SYNTHESIS January 2005 15

  • Organic Letters

    56156 Titanium catalysis in the Ugi reaction of -amino acids with aromatic aldehydesT. Godet, Y. Bovin, G. Vincent, D. Merle, A. Thozet, M. A. Ciufolini*, Org. Lett., 2004, 6(19), 3281-3284

    MeOH, rt, 12 h

    TiCl4

    16 amino acid and aryl aldehyde examples (7592%, 1.510 : 1 dr) 79%, 5 : 1 dr at *

    HOCO2H

    NH2

    HOMeO2C

    NH

    CONHtBu

    OMeMeOOMeMeO

    OHCNtBuC

    *

    56157 Copper-mediated cross-coupling reactions of N-unsubstituted sulfoximines and aryl halidesG. Y. Cho, P. Remy, J. Jansson, C. Moessner, C. Bolm*, Org. Lett., 2004, 6(19), 3293-3296

    DMSO, 90 C

    CuI

    18 examples (4895%) 72%

    IOMe

    PhSNH

    MeO Cs2CO3 OMe

    PhSN

    MeO

    56158 A highly diastereoselective MgI2-mediated ring expansion of methylenecyclopropanesM. E. Scott, W. Han, M. Lautens*, Org. Lett., 2004, 6(19), 3309-3312

    THF, reflux, 16 h

    MgI2

    13 examples (6594%, only one isomer observed in all but 2 examples) 82%, one isomer

    SN

    O

    N

    SN

    O

    N ONPh2

    O

    NPh2

    56159 Asymmetric transfer hydrogenation in water with a supported NoyoriIkariya catalystX. Li, X. Wu, W. Chen, F. E. Hancock, F. King, J. Xiao*, Org. Lett., 2004, 6(19), 3321-3324

    The catalyst could be reused more than 10 times with no loss in enantioselectivity

    water, 22 C, 18 h

    Ru-PTsDPEN

    16 examples (>87% yield, 8594% ee) 87% yield, 91% ee

    OO

    OOH

    Ru-PTsDPEN =

    NTsRu

    H2N

    O O

    Cl

    HCO2Na

    56160 Palladium-catalyzed dimerization disilylation of 1,3-butadiene with chlorosilanesJ. Terao, A. Oda, N. Kambe*, Org. Lett., 2004, 6(19), 3341-3344

    THF, 20 C

    Pd(acac)2

    7 examples (5793%, >78 : 22 E : Z) 88%, E isomer only

    Ph Si Cl SiMe2PhSiMe2Ph

    PhMgBr

    56161 Organic reactions in water: an efficient zinc-mediated stereoselective synthesis of (E)- and(Z)-trisubstituted alkenes using unactivated alkyl halidesB. Das*, J. Banerjee, G. Mahender, A. Majhi, Org. Lett., 2004, 6(19), 3349-3352

    Zn, sat. aq. NH4Cl

    21 examples (5886%, Z : E >80 : 20 for X = CN, 0 : 100 for X = CO2Me)

    OAcX I

    X

    X = CNX = CO2Me

    rt, 12 hrt, 10 h

    80%, 94 : 6 Z : E84%, 0 : 100 Z : E

    16 METHODS IN ORGANIC SYNTHESIS January 2005

  • Organic Letters

    56162 Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and baseN. A. Magomedov*, P. L. Ruggiero, Y. Tang, Org. Lett., 2004, 6(19), 3373-3375

    toluene, 23 C

    2,6-di-t-butylphenol,Me3Al, Et3N

    6 examples (7492%) 91%

    O

    SO2Ph

    OSO2Ph

    56163 ROMPgel-supported thiazolium iodide: an efficient supported organic catalyst for parallel Stetter reactionsA. G. M. Barrett*, A. C. Love, L. Tedeschi, Org. Lett., 2004, 6(19), 3377-3380

    DMF, 80 C, 20 h

    catalystcatalyst =

    15 examples (6899% yield, >66% purity) 95% yield, >95% purity

    O OO Ph

    N

    Sn

    INEt3

    OHC

    56164 Catalytic enantioselective conjugate addition of trimethylsilylacetylene to 2-cyclohexen-1-oneY.-S. Kwak, E. J. Corey*, Org. Lett., 2004, 6(19), 3385-3388

    tBuOMe, 0 C, 45 min O ONi

    catalyst =

    86% yield8288% ee

    O

    Me2Al SiMe3

    O

    SiMe3

    NN

    O OCN

    Ph Ph

    catalyst

    56165 Highly enantioselective dimerization of ,-enones catalyzed by a rigid quaternary ammonium saltF.-Y. Zhang, E. J. Corey*, Org. Lett., 2004, 6(19), 3397-3399

    The products could be converted to -chiral -keto acids by treatment with ozone, followed by hydrogen peroxide

    50% aq. KOH,toluene, 40 C, 12 h

    catalystcatalyst =

    7 examples (7981% yield, 8398% ee) 89% yield, 90% eeF

    O

    F

    O O

    FN

    NH

    H

    HOH

    Br

    56166 A 1,3-diaza-Claisen rearrangement that affords guanidinesA. M. Bowser, J. S. Madalengoitia*, Org. Lett., 2004, 6(19), 3409-3412

    CHCl3, rt

    EDCIEDCI =

    7 examples (6685%) 72%

    N

    Ph

    N NN

    C HClTs

    NH

    NH

    SN

    N

    NTs

    PhH

    H

    56167 Chiral norbornadienes as efficient ligands for the rhodium-catalyzed asymmetric 1,4-addition ofarylboronic acids to fumaric and maleic compoundsR. Shintani, K. Ueyama, I. Yamada, T. Hayashi*, Org. Lett., 2004, 6(19), 3425-3427

    dioxaneH2O, 50 C, 3 h

    [RhCl(C2H4)2]2, ligand ligand =

    8 examples (7795% yield, 6992% ee) 88% yield, 85% ee

    N

    O

    OF

    B(OH)2N

    O

    OF

    METHODS IN ORGANIC SYNTHESIS January 2005 17

  • Organic Letters

    56168 Azadiene DielsAlder cycloaddition of fulvenes: a facile approach to the [1]pyrindine systemB. Hong*, J. Wu, A. Gupta, M. Hallur, J. Liao, Org. Lett., 2004, 6(20), 3453-3456

    ClC6H5, microwave, 125 C, 0.337 h

    9 examples(2996% yield)

    87% yield

    +

    CO2Et

    NSO2Ph N

    H

    H

    CO2Et

    SO2Ph

    56169 Regioselective cross-metathesis reaction induced by steric hindranceS. BouzBouz*, R. Simmons, J. Cossy*, Org. Lett., 2004, 6(20), 3465-3467

    CH2Cl2, 40 C14 examples

    (2383% yield)80% yield

    +(5 mol%) Ru catalyst

    OTBDPS

    OMe

    OOMe

    O

    OTBDPS

    56170 One-pot homolytic aromatic substitutions/HWE olefinations under microwave conditions for the formationof a small oxindole libraryA. Teichert, K. Jantos, K. Harms, A. Studer*, Org. Lett., 2004, 6(20), 3477-3480

    2) microwave, 6 min, KOt-Bu, PhCHO

    13 examples(3587% yield)

    75% yield

    1) microwave, 2 min, DMF, 180 C, 0.03 MN

    PEtO

    O

    OEtO

    N

    O

    N

    OPh

    56171 Highly regioselective synthesis of tetrahydro-2H-1,3-thiazin-2-ones via rhodium-catalyzed carbonylationof N-alkylisothiazolidinesC. Dong, H. Alper*, Org. Lett., 2004, 6(20), 3489-3492

    (0.05 mmol) KI, toluene, CO (1000 psi), 24 h9 examples

    (3585% yield) 75% yield

    (0.05 mmol) [Rh(COD)Cl]2

    HS

    N n N

    S O H

    n

    56172 2-C-branched glycosides from 2-carbonylalkyl 2-O-Ms(Ts)-C-glycosides. A tandem SN2SN2 reaction via1,2-cyclopropanated sugarsH. Shao, S. Ekthawatchai, S. Wu, W. Zou*, Org. Lett., 2004, 6(20), 3497-3499

    K2CO3/MeOH, rt, overnight13 examples

    (5085% yield) 81% yield

    MeOHO

    BnOBnO

    BnO

    Me

    O

    OMsO

    BnOBnO

    BnO

    Me

    O

    56173 Cp*Ir complex catalyzed N-heterocyclization of primary amines with diols: a new catalytic system forenvironmentally benign synthesis of cyclic aminesK. Fujita*, T. Fujii, R. Yamaguchi*, Org. Lett., 2004, 6(20), 3525-3528

    NaHCO3, toluene, 110 C, 17 h14 examples

    (6394% yield) 91% yield

    [Cp*IrCl2]2NH2 + HO OH N

    18 METHODS IN ORGANIC SYNTHESIS January 2005

  • Organic Letters

    56174 Very efficient phosphoramidite ligand for asymmetric iridium-catalyzed allylic alkylationA. Alexakis*, D. Polet, Org. Lett., 2004, 6(20), 3529-3532

    NaHC(CO2Me)2, THF, 2565 C, 266 h20 examples

    (2199% yield1098% ee) 90% yield97% ee

    [IrCODCl]2ligandOCO2Me

    Cl

    CH(CO2Me)2

    +Cl

    Cl

    CH(CO2Me)2OO

    P N

    Me

    Me

    ligand =(6 examples)

    56175 Synthesis and trimethylaluminum additions on -hydroxy--sulfinyl and sulfonyl enoatesM. Carreno*, M. Sanz-Cuesta, F. Colobert*, G. Solladie*, Org. Lett., 2004, 6(20), 3537-3540

    CH2Cl2, 17 h, 0 C4 examples

    (9098% yield) 90% yield

    AlMe3p-Tol

    EtO

    O

    OH O

    p-Tol

    OOH

    OHMeMe

    56176 Palladium-catalyzed benzylation of active methine compounds without additional base: remarkableeffect of 1,5-cyclooctadieneR. Kuwano*, Y. Kondo, Org. Lett., 2004, 6(20), 3545-3547

    THF, 80 C, 372 h23 examples

    (71>99% yield) 84% yield

    Cp(3-C3H5)PdDPPF

    HOCOMe

    O +H C CO2Et

    CO2Et

    Ph H CO2Et

    CO2Et

    Ph

    56177 Synthesis of a new monodentate spiro phosphoramidite ligand and its application in Rh-catalyzedasymmetric hydrogenation reactionsS. Wu, W. Zhang, Z. Zhang, X. Zhang*, Org. Lett., 2004, 6(20), 3565-3567

    H2 (25 psi)8 examples

    (99.799.9% ee) 98.2% ee

    (0.001 mmol) [Rh(nbd)2]BF4-ligandCOOCH3

    NHAcH

    COOCH3

    NHAcH*

    56178 Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands forRh-catalyzed asymmetric hydrogenationX. Hu, Z. Zheng*, Org. Lett., 2004, 6(20), 3585-3588

    CH2Cl2, H2 (10 bar), rt, 0.51 h7 examples

    (10.699% ee) 99.6% ee

    Rh(COD)2BF4-ligand

    H

    HN

    O

    H

    HN

    O

    *

    ligand =(6 examples)

    O

    OPN

    PPh2

    Fe

    56179 Novel [2 + 2 + 2 + 1] cycloaddition of enediynes catalyzed by rhodium complexesB. Bennacer, M. Fujiwara, I. Ojima*, Org. Lett., 2004, 6(20), 3589-3591

    Cl(CH2)2Cl/toluene, CO (1 atm) 5080 C, 2136 h

    8 examples(1193% yield) 87% yield

    (5 mol%) [Rh(COD)Cl]2OMeOMeMeO

    MeO

    O

    MeOMeO

    OMeOMe

    METHODS IN ORGANIC SYNTHESIS January 2005 19

  • Organic Letters

    56180 A new ketone synthesis by palladium-catalyzed cross-coupling reactions of esters with organoboroncompoundsH. Tatamidani, F. Kakiuchi, N. Chatani*, Org. Lett., 2004, 6(20), 3597-3599

    dioxane, 50 C, 10 h14 examples

    (1697% yield)89% yield

    (0.03 mmol) Pd(OAc)2(0.09 mmol) PPh3OPy

    ClO

    Ph

    OCl

    56181 Highly enantioselective asymmetric hydrogenation of -acetamido dehydroamino acid derivatives using athree-hindered quadrant rhodium catalystH. Wu, G. Hoge*, Org. Lett., 2004, 6(20), 3645-3647

    solvent, H2 (650 psi), THF/MeOH, EtOAc

    7 examples(6699% ee)

    96% ee

    (1 mol%) Rh catalystCO2Et

    NHAcPr

    CO2Et

    NHAcPr

    56182 Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines,tetrahydro[1,8]napthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-onesE. Bacque, M. El Qacemi, S. Zard*, Org. Lett., 2004, 6(21), 3671-3674

    lauroyl peroxide, 1,2-dichloroethane,

    Numerous examples3799% yield

    R S O

    SN NCln

    Olauroyl peroxide, chlorobenzeneN NCl

    n

    O

    SR

    EtOS

    N NClO

    Rn

    56183 Highly efficient stereoconservative amidation and deamidation of -amino acidsD. Shendage, R. Frolich, G. Haufe*, Org. Lett., 2004, 6(21), 3675-3678

    ii) 1,4-dioxane, reflux, 5 h13 examples(098% yield)

    96% yield

    i) NaNO2, Ac2OAcOH (2 : 1),

    04 C, 1416 hPhtN

    NHMe

    O

    Me

    PhtNOMe

    O

    Me

    56184 Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-onesH. Imagawa, T. Kurisaki, M. Nishizawa*, Org. Lett., 2004, 6(21), 3679-3681

    C6H6, 0.520 h, rt9 examples

    (099% yield)98% yield

    (5 mol%) Hg(OTf)2O O

    56185 Stereoselective synthesis of multisubstituted butadienes through directed MizorokiHeck reaction andhomocoupling reaction of vinyl(2-pyridyl)silaneK. Itami*, Y. Ushiogi, T. Nokami, Y. Ohashi, J. Yoshida*, Org. Lett., 2004, 6(21), 3695-3698

    CH3CN, rt, 3 h15 examples

    (24>99% yield) 70% yield

    (11.2 equiv) CuI(1.31.5 equiv) CsF

    SiMe2Py

    S S

    S

    20 METHODS IN ORGANIC SYNTHESIS January 2005

  • Organic Letters

    56186 Racemic but tropos (chirally flexible) BIPHEP ligands for Rh(I)-complexes: highly enantioselectiveene-type cyclization of 1,6-enynesK. Mikami*, S. Kataoka, Y. Yusa, K. Aikawa, Org. Lett., 2004, 6(21), 3699-3701

    (20 mol%) TfOH, (CH2Cl2)2, 525 C, 0.519 h

    5 examples(2099% yield5694% ee)

    84% yield88% ee

    (10 mol%) catalyst

    Cl

    O

    Me

    ClMe

    O

    *

    N

    NH2

    H2

    PPh2

    PRh+

    Ph2

    Catalyst =

    56187 Preparation of tertiary amides from carbamoyl chlorides and organocupratesL. Lemoucheux, T. Seitz, J. Rouden*, M. Lasne, Org. Lett., 2004, 6(21), 3703-3706

    THF/Et2O, 300 C, 2 h19 examples

    (3090% yield) 85% yield

    (t-Bu)2CuLiLiCNN Cl

    O

    Nt-Bu

    O

    56188 Ring-closing metathesis of 2,2-divinylbiphenyls: a novel and general approach to phenanthrenesA. Luliano*, P. Piccioli, D. Fabbri, Org. Lett., 2004, 6(21), 3711-3714

    CH2Cl2/toluene, 25110 C, 224 h

    5 examples(0100% yield) 100% yield

    (10 mol%) catalyst

    H3CO

    Catalyst (2 examples)OCH3

    N N

    RuPCy3Cl

    Cl

    56189 Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging Suzuki couplingreactionsT. Colacot*, H. Shea, Org. Lett., 2004, 6(21), 3731-3734

    EtOHH2O, K2CO3,12 h, 80 C

    12 examples(0100% yield)

    93% yield

    (0.01 eq.) catalystCatalyst (7 examples)

    FBr

    MeO

    PhB(OH)2 + FPh

    MeO

    PPd

    Pt-Bu2

    Cl

    Clt-Bu2

    56190 Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenolswith silylaryl triflatesZ. Liu, R. Larock*, Org. Lett., 2004, 6(21), 3739-3741

    MeCN, CsF, 100 C, 24 h

    10 examples(6687% yield)

    85% yield

    (10 mol%) PCy3(5 mol%) Pd(OAc)2

    OH

    IMeO2C O

    MeO2C

    METHODS IN ORGANIC SYNTHESIS January 2005 21

  • Organic Letters

    56191 An efficient synthesis of -C-glycosides based on the conformational restriction strategy: Lewis acidpromoted silane reduction of the anomeric position with complete stereoselectivityM. Terauchi, H. Abe, A. Matsuda, S. Shuto*, Org. Lett., 2004, 6(21), 3751-3754

    CH2Cl2, 78 C, 60 min

    13 examples(5395% yield)

    90% yield

    Et3SiH, TMSOTfOOBn

    Ph

    OHBnO

    OO

    MeO

    OMe

    OOBn

    PhBnO

    OO

    MeO

    OMe

    56192 Regioselective enzymatic acylation of -L-2-deoxynucleosides: application in resolution of-D/L-2-deoxynucleosidesJ. Garcia, S. Fernandez, M. Ferrero, Y. Sanghvi, V. Gotor*, Org. Lett., 2004, 6(21), 3759-3762

    THF, 30 C, 0.5192 h

    4 examples(1495% yield

    >99% ee)90% yield>99% ee

    lipaseLevO

    NO OHT

    OH

    +

    O OLevT

    OH

    56193 Enantioselective aldol reaction of trimethoxysilyl enol ether catalyzed by lithium binaphtholateM. Nakajima*, Y. Orito, T. Ishizuka, S. Hashimoto, Org. Lett., 2004, 6(21), 3763-3765

    H2O, THF, 23 C, 0.5 h

    11 examples(7598% yield

    897% ee (syn)095% ee (anti))

    94% yield>97% ee (syn)84% ee (anti)

    (10 mol%) catalyst

    CHO

    +

    OSi(OMe)3 O OH catalyst =Br

    OLiOLi

    Br

    56194 Efficient and selective removal of methoxy protecting groups in carbohydratesA. Boto*, D. Hernandez, R. Hernandez, E. Suarez, Org. Lett., 2004, 6(21), 3785-3788

    (diacetoxyiodo)benzene, I2, CH2Cl2, 25 C, h (80 w)

    7 examples(5190% yield)

    82% yield

    OMeO OH

    OMeOMe

    MeOO

    O

    OMeOMe

    MeO+

    O

    OO OH

    OMeOMe

    MeO

    AcO

    56195 Environmentally benign synthesis of H-phosphonic acids using a water-tolerant, recyclablepolymer-supported catalystS. Deprele, J. Montchamp*, Org. Lett., 2004, 6(21), 3805-3808

    H3PO2, CH3CN, N2, refluxrt, 312 h, 15 runs

    12 examples(4292% yield)

    91% yield

    (0.5 mol%) Pd catalystCl Cl PO2H2 N ONH

    O PPh2

    PPh2

    Pd

    Catalyst =

    22 METHODS IN ORGANIC SYNTHESIS January 2005

  • Synthesis

    56196 Application of phosphineoxazoline ligands in Ir-catalyzed asymmetric hydrogenation of acyclic aromaticN-aryliminesA. Trifonova, J. Diesen, C. Chapman, P. Andersson*, Org. Lett., 2004, 6(21), 3825-3827

    CH2Cl2, N2 (20 bar), rt

    9 examples(099% conversion

    6696% ee)98% conversion

    90% ee

    (0.5 mol%) catalyst

    Catalyst (2 examples) =

    MeO

    N

    MeO

    HN

    *

    N

    Ph

    IrPh

    O

    N

    i-PrH

    56197 An ionic liquid-coordinated palladium complex: a highly efficient and recyclable catalyst for the HeckreactionJ. Xiao, B. Twamley, J. Shreeve*, Org. Lett., 2004, 6(21), 3845-3847

    ionic liquid, NaCO3, 100 C, 4 h3 examples

    (7094% yield)83% yield

    (2 mol%) PdCl2Cl + Ph

    Ph

    56198 Chiral [2.2.2] dienes as ligands for Rh(I) in conjugate additions of boronic acids to a wide range ofacceptorsC. Defieber, J. Paquin, S. Serna, E. Carreira*, Org. Lett., 2004, 6(21), 3873-3876

    KOH, dioxane/H2O, 118 h, 50 C16 examples

    (4398% yield8898% ee)

    93% yield88% ee

    (1.5 mol%) [Rh(C2H4)2Cl]2+ PhB(OH)2MeO

    O

    MeO

    O Ph

    56199 Synthesis of seven-membered ring glycals via endo-selective alkynol cycloisomerizationE. Alcazar, J. Pletcher, F. McDonald*, Org. Lett., 2004, 6(21), 3877-3880

    ii) Ac2O, DMAP

    9 examples(1796% yield) 81% yield

    i) (15%) W(CO)6, Et3N, THF,h (350 nm), 5570 C, 6 hO

    OMe

    Me

    HOH

    HOO

    AcO

    O O

    Synthesis

    56200 Iodine catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones: a simple and efficientprocedure for the Biginelli reactionK. V. N. S. Srinivas, B. Das*, Synthesis, 2004, (13), 2091-2093

    CH3CN, reflux, 7 h

    86%29 substrates (7293%)

    I2

    CH3

    H

    O

    H3C OCH2CH3

    O O+ +

    H2N NH2

    O

    NH

    NH

    H3C

    H3CH2CO

    O

    CH3

    METHODS IN ORGANIC SYNTHESIS January 2005 23

  • Synthesis

    56201 Simple and improved procedure for the regioselective acylation of aromatic ethers with carboxylic acidson the surface of graphite in the presence of methanesulfonic acidM. H. Sarvari, H. Sharghi*, Synthesis, 2004, (13), 2165-2168

    010 C, 20 min

    98%12 substrates (8098%)

    GraphiteMeSO3H+ MeCO2H

    OMe

    MeO

    O

    Me

    56202 An improved catalytic system, Pd(PPh3)4/PhCOOH combined catalyst, for the allylation of carbonpronucleophiles with allenesN. T. Patil, N. K. Pahadi, Y. Yamamoto*, Synthesis, 2004, (13), 2186-2190

    1,4 dioxane, 100 C, 12 h90%10 examples (7090%)

    Pd(PPh3)4, PhCOOH+C C CH2

    H

    Ph

    COOEt

    COOEt

    PhCOOEt

    COOEt

    56203 A novel four-component reaction for the diastereoselective synthesis of some new spiro pyrrolizidinesvia 1,3-dipolar cycloaddition of azomethine ylidesJ. Azizian*, A. R. Karimi, A. A. Mohammadi, M. R. Mohammadizadeh, Synthesis, 2004, (14), 2263-2265

    Reaction proceeds to 7686% yields under reflux for 23 h.

    DMSO, 35 min

    89%6 examples (8795%)

    MW

    +

    O

    O

    OHOH

    NH2

    NH2

    +

    NH

    CO2H

    O

    O

    Cl

    +

    N

    N

    N N

    O

    O

    Cl

    H

    H

    +

    56204 Highly efficient double-activation catalysts for the synthesis of ketone cyanohydrinsF.-X. Chen, X. Liu, B. Qin, H. Zhou, X. Feng*, G. Zhang, Synthesis, 2004, (14), 2266-2272

    rt, 13 h

    99%13 examples (8499%)

    AlEt3, [L]+

    O

    N

    ONC O Si

    OH

    N N

    HO

    [L] =

    56205 Ionic liquids promoted multi-component reaction: green appraoch for highly substituted 2-aminofuranderivativesJ. S. Yadav*, B. V. S. Reddy, S. Shubashree, K. Sadashiv, J. J. Naidu, Synthesis, 2004, (14), 2376-2380

    rt, 2 h

    84%12 examples (7889%)

    [bmim]BF4+

    MeOOC

    COOMe

    H

    O

    +

    NC

    O NH

    MeO2C CO2Me

    56206 A new reactive system for HornerWadsworthEmmons olefination of optically active4-hydroxy-2-oxo-alkylphosphonates and 4-hydroxy-1-1chloro-2-oxo-alkylphosphonates with aliphaticaldehydesC. Xu, C. Yuan*, Synthesis, 2004, (15), 2449-2458

    H2O, THF94%, >99% ee26 examples (7696%, 95>99% ee)

    K2CO3+

    PhP(OEt)2

    OOH OEtCHO

    Ph

    OOH

    Et

    24 METHODS IN ORGANIC SYNTHESIS January 2005

  • Synthesis

    56207 TFFH as an excellent reagent for acylation of alcohols, thiols and dithiocarbamatesM. Pittelkow, F. S. Kamounah, U. Boas, B. Pedersen, J. B. Christensen*, Synthesis, 2004, (15), 2485-2492

    DMAP, rt, over night

    97%20 examples (3897%)

    TFFH+

    OH

    O

    HO O

    O

    TFFH = N NF PF6

    56208 Bi(OTf)3 as novel and efficient catalyst for the stereoselective synthesis of C-pseudoglycalsJ. S. Yadav*, B. V. S. Reddy, K. S. Reddy, L. Chandraiah, V. Sunitha, Synthesis, 2004, (15), 2523-2526

    MeCN, rt, 15 min

    95%10 examples (8795%)

    Bi(OTf)3+

    OAcO

    OAcAcO

    TMSOAcO

    AcO

    56209 Novel synthetic strategy of N-arylated heterocycles via sequential palladium-catalyzed intra- andinter-arylamination reactionsR. Omar-Amrani, R. Schneider*, Y. Fort*, Synthesis, 2004, (15), 2527-2534

    NaH, tBuOH, 1,4-dioxane, 100 C, 8 h

    92%19 examples (4199%)

    Pd(OAc)2+

    Cl

    NH2Cl

    N

    56210 Facile synthesis of 2,3-disubstituted quinoxalines by SuzukiMiyaura couplingL. Mao, H. Sakurai*, T. Hirao*, Synthesis, 2004, (15), 2535-2539

    K2CO3, tolueneethanol, reflux, 48 h

    92%14 examples (7796%)

    Pd(PPh3)4+ PhB(OH)2NN

    Cl Cl

    NN

    Ph Ph

    56211 The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazolesY. Tang, Y. Dong, J. L. Vennerstrom*, Synthesis, 2004, (15), 2540-2544

    MeCN, rt, 2 h

    100%28 examples (10100%)

    Carbonyl diimidazoleO

    O OH

    O

    O

    OO

    N

    N

    56212 Unexpected addition of methyl 3,3,3-trifluoropyruvate to push-pull enamines having a methyl group at-positionD. M. Volochnyuk, A. N. Kostyuk*, D. A. Sibgatulin, A. E. Petrenko, Synthesis, 2004, (15), 2545-2549

    Benzene, rt, several hours

    84%12 examples (5398%)

    F3C OMeO

    O

    +

    (H2C)4NCN

    Me

    (H2C)4NCN

    CO2Me

    F3C

    HO

    METHODS IN ORGANIC SYNTHESIS January 2005 25

  • Synthesis

    56213 The first synthesis of 1,1-dinitrocyclopropaneE. M. Budynina, E. B. Averina, O. A. Ivanova, N. V. Yashin, T. S. Kuznetsova*, N. S. Zefirov, Synthesis, 2004, (16), 2609-2610

    benzene, 5 CHC(NO2)3

    CH2N2NO2NO2

    +O

    N

    NO2

    O

    62% 23%

    56214 The Huisgen reaction of azomethane ylide to isatins: a facile synthesis of spiro-oxindolesV. Nair*, S. Mathai, A. Augustine, S. Viji, K. V. Radhakrishnan, Synthesis, 2004, (16), 2617-2619

    CH2Cl2, rt, 3 h

    TFA+

    82%

    MeSi N

    MeMe

    Ph

    OMe N

    O

    O

    MeN

    O

    Me

    NO

    56215 Stereoselective reduction of -hydroxy -ketoesters: a concise synthesis of anti-,-dihydroxy estersM. Liao, W. Yao, J. Wang*, Synthesis, 2004, (16), 2633-2636

    CH2Cl2, 63 C to rt, 8 h

    NaBH4

    11 examples, 6086%

    Ph OEt

    OH

    O

    O

    Ph OEt

    OH

    OH

    O

    56216 A tandem nucleophilic addition, defluorination and destannylation. Stereospecific syntheses oftrifluoromethylated alkyl and aryl vinyl ethersY. Shen*, G. Wang, Synthesis, 2004, (16), 2637-2640

    45 h, MeOH or EtOH, reflux

    CH3ONa

    7 examples, 7395%

    SnBu3

    F3-CH3C6H4

    F3C H

    OCH33-CH3C6H4

    F3C

    56217 Environmentally benign preparation of heteroaromatics from ketones or alcohols, with macroporouspolystyrenesulfonic acid and (diacetoxyiodo)benzene, followed by thioamide, amidine, and2-aminopyridineM. Weno, H. Togo*, Synthesis, 2004, (16), 2673-2677

    CH3CN, reflux, 24 h

    K2CO3

    20 examples, 3193%

    S OO

    OIPh

    OHN NH2 Ph

    O+ +

    N

    OPh

    56218 Reactions of 1,4-benzodiazepinic N-nitrosoamides with tosylmethyl isocyanide: a novel synthesis ofmidazolamC. del Pozo*, A. Macias, E. Alonso, J. Gonzalez*, Synthesis, 2004, (16), 2697-2703

    78 C

    BuLi

    5 examples6882%

    N

    NN

    Cl

    NOMe

    F

    Me

    SO2CH2CN

    + N

    N

    Cl

    F

    NTos

    26 METHODS IN ORGANIC SYNTHESIS January 2005

  • Synthetic Communications

    Synthetic Communications

    56219 Infrared irradiation: effective promoter in the formation of N-benzylideneanilinesM. A. Vazquez, M. Landa, L. Reyes, R. Miranda, J. Tamariz, F. Delgado*, Synth. Commun., 2004, 34(15), 2705-2718

    10 min, no solvent

    26 examples (4597%) 95%

    IR

    Me2N

    H

    O NH2

    Me2N

    H

    N

    56220 A mild and efficient method for cleavage of C1N using imidazolium dichromateS. K. De*, Synth. Commun., 2004, 34(15), 2751-2755

    imidazolium dichromateMeCN, reflux, 6 h

    17 examples (8294%) 94%

    NPh

    PhOH O

    Ph

    Ph

    56221 Highly regioselective ring opening of epoxides with polymer supported phenoxide and naphthoxide anionsB. Tamami*, N. Iranpoor, R. Rezaei, Synth. Commun., 2004, 34(15), 2789-2795

    ethanol50 C, 1.5 h

    28 examples (3096%) 96%

    OO

    O OOH

    C6H4CH2N(CH3)3OC6H5CH3

    Me2HC

    Me2HC

    56222 Titanium dioxide as a mild and efficient catalyst for conversion of epoxides to thiiranesB. Yadollahi*, S. Tangestaninejad, M. H. Habibi, Synth. Commun., 2004, 34(15), 2823-2827

    TiO2, NH4SCNMeCN, reflux, 40 min

    7 examples (8996%) 96%

    O

    OPh

    S

    OPh

    56223 Oxidation of benzylic alcohols to carbonyl compounds with potassium permanganate in ionic liquidsA. Kumar, N. Jain, S. M. S. Chauhan*, Synth. Commun., 2004, 34(15), 2835-2842

    KMnO4, [bmim][BF4]rt, 1 h

    12 examples (8597%) 97%

    MeO CH2OH MeO CHO

    56224 Potassium fluoride assisted selective acetylation of alcohols with acetic acidJ. W. J. Bosco, B. R. Raju, A. K. Saikia*, Synth. Commun., 2004, 34(15), 2849-2855

    80 C, 1.5 h

    17 examples (3499%) 98%

    KFOH OAcMeCO2H

    56225 Selective reduction of aldehydes to alcohols using alumina with a catalytic amount of base undermicrowave irradiationP. K. Pradhan, P. Jaisankar, B. Pal, S. Dey, V. S. Giri*, Synth. Commun., 2004, 34(15), 2863-2872

    Al2O3, DMAPMW 300 W (2 x 5 min), MeOH

    11 examples (8095%) 95%

    OHC NO2 HOH2C NO2

    METHODS IN ORGANIC SYNTHESIS January 2005 27

  • Synthetic Communications

    56226 Regioselective synthesis of chromeno[4,3-c] isoquinolin-11-ones by radical cyclizationK. C. Majumdar*, S. Sarkar, Synth. Commun., 2004, 34(16), 2873-2883

    Bu3SnCl3, Na(CN)BH3AIBN, C6H6, reflux, 34 h, N2 atmosphere

    O

    MeN

    Me3C

    O

    Br

    O

    Me3C

    O8 examples6568%

    56227 An eco-friendly synthesis of electrophilic alkenes catalyzed by dimethylaminopyridine under solvent-freeconditionsA. V. Narsaiah, A. K. Basak, B. Visali, K. Nagaiah*, Synth. Commun., 2004, 34(16), 2893-2901

    DMAP

    8085 C, 2.54 h15 examples7595%

    CHO+

    CN

    CO2Et

    CO2Et

    CN

    56228 Selective thioacetalization of aldehydes catalyzed by aqueous zinc tetrafluoroborateS. Islam, A. Majee*, T. Mandal, A. T. Khan, Synth. Commun., 2004, 34(16), 2911-2916

    CH2Cl2, rt, 5900 min

    21 examples7095%

    +

    CHOHS

    SH HCS

    SZn(BF4)

    56229 Direct synthesis of N-acylalkylenediamines from carboxylic acids under mild conditionsB. P. Bandgar*, S. V. Bettigeri, Synth. Commun., 2004, 34(16), 2917-2924

    triphenylphosphine, NBS2555 min, DCM

    21 examples7797%

    CH3(CH2)2COOH + HN NH

    O

    NCH3(CH2)NH

    56230 A convenient preparation of enantiopure endo-2-hydroxyepicamphor and endo-3-hydroxycamphor fromcamphoric acidQ. Tan, D. Li, H. Bao, Y. Wang, J. Wen, T. You*, Synth. Commun., 2004, 34(16), 2945-2950

    The starting compound is easily prepared from camphoric acid

    MeOH, N2, 25 C, 12 h; or THF, HCl, 25 C

    2 examples7191%

    OSiMe3

    OSiMe3

    OH

    O

    H

    56231 N-methylmorpholine N-oxide: a rare nonmetallic catalyst for the most efficient silylcyanation of aldehydesS. S. Kim*, G. Rajagopal, D. W. Kim, D. H. Song, Synth. Commun., 2004, 34(16), 2973-2980

    1030 min, CH2Cl2

    12 examples7598%

    Me3SiCN, N-methylmorpholine N-oxide

    H

    O

    CN

    OSiMe3

    28 METHODS IN ORGANIC SYNTHESIS January 2005

  • Synthetic Communications

    56232 Synthesis of diacetals from aldehydes and ketones with pentaerythritol catalyzed by silica sulfate undermicrowave irrradiationT.-S. Jin*, H.-X. Wang, K.-F. Wang, T.-S. Li, Synth. Commun., 2004, 34(16), 2993-2999

    benzene or toluene, 0.55.0 h

    17 examples8098%

    silica sulphate, hH

    O O

    O

    O

    O

    56233 One-pot syntheses of amides from N-acylation of nitroarenes with esters mediated by samarium diiodideX. Wang*, H. Guo, G. Xie, Y. Zhang, Synth. Commun., 2004, 34(16), 3001-3008

    THF, rt

    11 examples8295%

    NO2+ C

    OOCH2CH3H3C

    HN

    CCH3

    O

    SmI2

    56234 Synthesis of N,N-bis(2-thiazolinyl)-, N,N-bis(2-thiazolyl)-, and N,N-bis(2-pyrimidinyl)-benzenedicarboxamidesS. R. Gondi, D. Y. Son*, Synth. Commun., 2004, 34(17), 3061-3072

    124 h,

    EtOAcMeOHNS

    NH2

    +

    COCl

    COCl

    COHN

    COHN

    S

    N

    S N 10 examples3484%

    56235 Zirconium(IV) chloride catalyzed cyclization of ortho-allylphenols: synthesis of2-methyl-2,3-dihydrobenzofuransH. M. Meshram*, K. Premalatha, K. Rameshbabu, B. Eeshwaraiah, J. S. Yadav, Synth. Commun., 2004, 34(17), 3091-3097

    820 h, DCM, 0 C rt, N2 atmosphere

    ZrCl4

    10 examples6085%OH

    CH2HC

    COMe

    CH2

    MeOC

    O

    56236 Efficient synthesis of 3-substituted coumarinsS. H. Mashraqui*, D. Vashi, H. D. Mistry, Synth. Commun., 2004, 34(17), 3129-3134

    CH3CN, , N2, reflux, 28 h

    2-chloro-1-methylpyridinium iodide(C2H5)3N

    13 examples6391%

    CHO

    OH+

    CH2CO2H

    O O

    56237 Silica-supported sodium hydrogen sulfate catalyzed facile transformation of p-hydroxybenzyl alcohols top-hydroxybenzyl ethers and thioethersR. Ramu, N. R. Nath, M. R. Reddy, B. Das*, Synth. Commun., 2004, 34(17), 3135-3145

    1.52 h, rtNaHSO4/SiO2

    21 examples8095%

    +

    HO

    OHOH

    HO

    OMe

    METHODS IN ORGANIC SYNTHESIS January 2005 29

  • Synthetic Communications

    56238 Trimethylsilyl chloride: a facile and efficient reagent for one-pot synthesis of3,4-dihydropyrimidin-2(1H)-onesY. Zhu, Y. Pan*, S. Huang, Synth. Commun., 2004, 34(17), 3167-3174

    rt, DMFCH3CN, 13 h

    TMSCl

    28 examples7697%

    +OC2H5

    O O

    H2N NH2

    O+ C6H5CHO H5C2O

    NH

    NH

    O C6H5

    O

    56239 Facile and efficient deoxygenation of amine-N-oxides with gallium in waterJ. H. Han, K. I. Choi, J. H. Kim, B. W. Yoo*, Synth. Commun., 2004, 34(17), 3197-3201

    0.524 h, reflux, H2O

    Ga

    9 examples8195%

    N

    CN

    ON

    CN

    56240 A facile synthesis of 4-Ar-2-bromopyridine and its 2,2-bipyridine derivativesX.-F. Duan*, X.-H. Li, F.-Y. Li, C.-H. Huang, Synth. Commun., 2004, 34(17), 3227-3233

    THF, 40 C, Pd(PPh3)4

    4-CH3C6H4MgBr

    3 examples4570%N

    I

    N

    4-CH3C6H4

    Br Br

    56241 A novel route to 3-(O,O-diethylphosphoryl)-2,3-dihydrofurans via rhodium-catalyzed heterocycloadditionreactionD. Ging, L. Zhang, C. Yuan*, Synth. Commun., 2004, 34(18), 3251-3258

    85 CH3CP

    OEt

    O

    N2

    OOEt Rh2(OAc)4Et

    O+ O N

    Et

    H3C P(O)(OEt)2

    5 examples7690%

    56242 Nitration of cinnamic acids using cerium(IV) ammonium nitrate immobilized on silicaA. Messere, A. Gentili, I. Garella, F. Temussi, B. Di Blasio, A. Fiorentino*, Synth. Commun., 2004, 34(18), 3317-3324

    TFA, MgSO4, rt, 20 min

    CeNH4(NO2)5/SiO2

    3 examples5790%

    HO

    COOH

    HO

    COOH

    NO2

    56243 Microwave-assisted synthesis of dihydropyrimidines in solvent-free conditionM. Mirza-Aghayan*, M. Bolourtchian, M. Hosseini, Synth. Commun., 2004, 34(18), 3335-3341

    The reaction proceeds in solvent-free conditions.

    2030 s, h

    FeCl36H2O

    8 examples3868%

    O

    + Me OEt

    O O

    + H2N NH2

    O

    NH

    NEtO

    O

    Me O

    H

    30 METHODS IN ORGANIC SYNTHESIS January 2005

  • Synthetic Communications

    56244 Nickel-catalyzed electrochemical synthesis of dihydro-benzo[b]thiophene derivativesJ. Pelletier, S. Olivero, E. Dunach*, Synth. Commun., 2004, 34(18), 3343-3348

    CH3CN, electrolysis

    Ni(cyclam)(BF4)25 examples5973%

    Br

    S S

    56245 Improved synthesis of 7-(alkyl/aralkyl)guaninesA. Vidal*, I. Giraud, J.-C. Madelmont, Synth. Commun., 2004, 34(18), 3359-3365

    DMA or acetic acid, HCl, 148 h, rt120 C

    alkylating agent (e.g. CH3CH2I, 11 examples)

    11 examples5197%

    O

    HO OH

    HON

    N N

    NH

    O

    NH2N

    N N

    NH

    O

    NH2

    CH3H2C

    HCl

    56246 Synthesis of iodinated naphthoquinones using morpholineiodine complexA. L. Perez*, G. Lamoureux, A. Herrera, Synth. Commun., 2004, 34(18), 3389-3397

    rt, pH 2, 1060 min

    K2CO3 H2O or dichloroethane

    3 examples5587%

    OOH

    O

    +O

    N IH

    I

    OOH

    OI

    56247 RuCl3 catalyzed facile conversion of arylalkyl ketoximes to amidesS. K. De*, Synth. Commun., 2004, 34(18), 3431-3434

    reflux, CH3CN, 1.59 h

    RuCl3

    11 examples4891%

    NH3C

    H5C6

    OHC6H5NHCOCH3

    56248 Synthesis of fused imidazoles based on -bromodypnoneV. Kovtunenko*, L. Potikha, A. Turov, Synth. Commun., 2004, 34(19), 3069-3613

    benzene, reflux+

    OPh

    Ph

    Br N

    N NH2

    N

    N NH

    Ph

    PhO

    Br

    56249 A rapid and convenient synthesis of homallylic alcohols by the BarbierGrignard reactionG. J. Sormunen, D. E. Lewis*, Synth. Commun., 2004, 34(19), 3473-3480

    Mg

    Et2OO

    C10H7+ Br

    HO

    H7C107 examples3482%

    56250 The synthesis of 9,10-dihydro-9,10-(methaniminomethano)anthracene and N-protected derivatives viadouble reductive aminationP. Stoy, J. Rush, W. H. Pearson*, Synth. Commun., 2004, 34(19), 3481-3489

    PMBNH2, NaBH3CN

    78 or 6080 C, MeOH

    4 examples4093%

    CHO

    CHO

    PMP-N

    METHODS IN ORGANIC SYNTHESIS January 2005 31

  • Synthetic Communications

    56251 Novel and efficient method to synthesize N-benzyl-4-formyl-piperidineR. Sheng, Y. Hu*, Synth. Commun., 2004, 34(19), 3529-3533

    MgBr2Et2O

    NaOH, 2080 C3886%

    H2C N O

    H2C N H

    O

    + (CH3)3S+IO

    56252 Novel synthesis of 2-oxo-2H-benzopyrano[2,3-d]pyrimidinesH. Turki, S. Abid, Y. le Bigot, S. Fery-Forgues, R. El Gharbi*, Synth. Commun., 2004, 34(19), 3553-3563

    215 h, 65 C, MeOH

    6 examples2088%

    +

    O

    NEt

    Et

    CN

    N COEt

    OEt CH2NH2

    NEt

    EtO

    N

    NNHCH2

    O

    56253 Efficient tetrahydropyranylation of alcohols and detetrahydropyranylation reactions in the presence ofcatalytic amount of trichloroisocyanuric acid (TCCA) as a safe, cheap industrial chemicalH. Firouzabadi*, N. Iranpoor*, H. Hazarkhani, Synth. Commun., 2004, 34(19), 3623-3630

    MeOH, TCCA, rt, 38 h

    dihydropyran, 6080 C, 548 hOH O

    33 examples7595%

    33 examples9096%

    TCCA: trichloroisocyanuric acid

    N N

    NCl

    O

    ClO

    Cl

    O

    56254 -PCC and -PCC-SiO2 as efficient reagents for oxidation of thiols to disulfidesM. M. Khodaei*, P. Salehi, M. Goodarzi, A. Yazdanipour, Synth. Commun., 2004, 34(20), 3661-3666

    -PCC-SiO2CH2Cl2, rt, 4 h

    12 substrate examples (3895%) 95%

    CH2SH

    56255 Potassium dodecatungstocobaltate trihydrate (K5CoW12O403H2O) as an efficient catalyst for aminolysisof epoxidesE. Rafiee*, S. Tangestaninejad, M. H. Habibi, V. Mirkhani, Synth. Commun., 2004, 34(20), 3673-3681

    MeCN, reflux, 5.5 h90 examples (4599%) 99%

    K5CoW12O403H2OOCl H2N Br

    OH

    CH2ClNHBr

    56256 Efficient and selective formation of mixed acetals by Nafion-H SAC-13 silica nanocomposite solid acidcatalystI. Ledneczki, A. Molnar*, Synth. Commun., 2004, 34(20), 3683-3690

    reflux, 5 min32 examples (up to 100%) 100%

    SAC-13OH (BuO)2CH2 O

    CH2OBu

    56257 Stereoselective synthesis of cis-1-aryl-2-benzoyl-3,3-dicyanocyclopropanes in the presence of KF2H2OZ. Ren*, W. Cao, W. Ding, Y. Wang, L. Wang, Synth. Commun., 2004, 34(20), 3785-3792

    DME, rt, 4 h

    11 examples (8695%) 95%

    KF2H2OC6H5CH C(CN)2CN

    CNC6H5

    COPh

    Ph3AsCH2COPhBr

    32 METHODS IN ORGANIC SYNTHESIS January 2005

  • Tetrahedron

    56258 Microwave-induced rapid access to aromatic and heteroaromatic sulfonamides under solvent-freeconditions without using external baseA. K. Sharma, S. K. Das*, Synth. Commun., 2004, 34(20), 3807-3819

    6 min

    28 examples (3094%) 94%

    MW

    NH2

    Br Br

    HN

    SMeSO2Cl

    Ph

    O O

    56259 Bismuth subnitrate catalyzed efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones: an improvedprotocol for the Biginelli reactionY. T. Reddy, B. Rajitha*, P. N. Reddy, B. S. Kumar, V. P. Rao, Synth. Commun., 2004, 34(20), 3821-3825

    MeCN, 7080 C, 1.5 h

    17 examples (8896%) 96%

    BiONO3O O

    Ph H NH2 NH3 Me OMe

    O O

    NH

    N

    Ph

    O

    O

    MeO

    Tetrahedron

    56260 Calcium phosphate-vanadate apatite (CPVAP)-catalyzed aerobic oxidation of propaygylic alcohols withmolecular oxygenY. Maeda, Y. Washitake, T. Nishimura*, K. Iwai, T. Yamauchi, S. Uemura*, Tetrahedron, 2004, 60(41), 9031-9036

    n-PrCN, 100 C, 20 h, O2 (1 atm)

    99%18 substrates (2099%)

    Calcium phosphate vanadate apatite

    Me

    OH

    Me

    O

    56261 Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylatedoctahydrobinaphthyl-2,2-diamine ligandK. H. Kim, D.-W. Lee, Y.-S. Lee, D.-H. Ko, D.-C. Ha*, Tetrahedron, 2004, 60(41), 9037-9042

    CH2Cl2

    98%, 42% ee15 examples (5699%)

    CuCl, O2, mol sieves, [N]CO2Me

    OH

    CO2Me

    OH

    CO2Me

    OH

    NH2NH2

    [N] =

    56262 Scope and limitation of montmorillonite K 10 catalysed opening of epoxide rings by amineA. K. Chakraborti*, A. Kondaskar, S. Rudrawar, Tetrahedron, 2004, 60(41), 9085-9091

    rt, 3 h

    98%16 substrates (69100%)

    Montmorillonite K 10O

    NH2

    +

    HO HN

    METHODS IN ORGANIC SYNTHESIS January 2005 33

  • Tetrahedron

    56263 -Hydroxy carboxylic acids as ligands for enantioselective diethylzinc additions to aromatic and aliphaticaldehydesT. Bauer*, J. Gajewiak, Tetrahedron, 2004, 60(41), 9163-9170

    Et2Zn, 28 C, 19 h97%, 77% ee18 substrates (7097%, 5283% ee)

    H3CO CHO H3COOH

    OH

    O

    HO

    Ph

    56264 Enantioselective total synthesis of ()-strychnine: development of a highly practical catalytic asymmetriccarboncarbon bond formation and domino cyclizationT. Ohshima, Y. Xu, R. Takita, M. Shibasaki*, Tetrahedron, 2004, 60(43), 9569-9588

    KO-t-Bu THF, rt, 4 mol sieve

    95%, >99% ee9 examples (7496%, 93>99% ee)

    [Al]+

    CO2Me

    O CO2MeO

    CO2Me

    CO2MeH

    OO

    AlOO

    Li[Al] =

    56265 Sequential ring-closing metathesis/Pd-catalyzed, Si-assisted cross-coupling reactoins: general synthesisof highly substituted unsaturated alcohols and medium-sized rings containing a 1,3-cis-cis diene unitS. E. Denmark*, S.-M. Yang, Tetrahedron, 2004, 60(43), 9695-9708

    rt, 30 min

    92%11 examples (9193%)

    TBAF, Pd(dba)2Si

    O

    Me Me OH

    I

    OMe+

    56266 Combinatorial approach to the asymmetric hydrogenation of -acylamino acrylates: use of mixtures ofchiral monodentate P-ligandsM. T. Reetz*, X. Li, Tetrahedron, 2004, 60(43), 9709-9714

    CH2Cl2

    92%171 examples (8.3100%, 13.498.8% ee)

    L2Rh(COD)BF4R'

    HNO

    CO2R''

    R' = CH3, C2H5, n-C3H7, C6H5R'' = CH3, C2H5

    R'

    HNO

    CO2R''

    L = chiral monodentate P ligands

    56267 Palladium-catalyzed -arylation of N-protected 2-piperidinonesA. de Filippis, D. G. Pardo, J. Cossy*, Tetrahedron, 2004, 60(43), 9757-9767

    THF, 65 C

    97%38 examples (099%)

    Pd(dba)2, [L][L] =N

    BnO Br

    NBn

    O

    +NH2

    Cy2P

    56268 Highly diastereo- and enantioselective reactions of enecarbamates with an aldehydeR. Matsubara, P. Vital, Y. Nakamura, H. Kiyohara, S. Kobayashi*, Tetrahedron, 2004, 60(43), 9769-9784

    CH2Cl2

    95%, 98% ee17 examples (8297%, 9498% ee)

    CuClO44CH3CN, [L][L] =

    +

    O

    EtOO

    H HN

    Ph

    O

    OBnMe

    O

    EtOOH

    Me

    N

    Ph

    O

    OBnN N

    p-Br-C6H4 p-Br-C6H4

    34 METHODS IN ORGANIC SYNTHESIS January 2005

  • Tetrahedron Letters

    Tetrahedron Letters

    56269 Palladium-catalysed three component synthesis of ,-unsaturated amidines and imidatesK. Kishore, R. Tetela, R. J. Whitby*, M. E. Light, M. B. Hurtshouse, Tetrahedron Lett., 2004, 45(38), 6991-6994

    tBuNCPdCl2, dppf, Cs2CO3, 65 C, toluene, 1530 min

    PhBr NH

    Ph N

    NtBu

    56270 Palladium catalysed synthesis of cyclic amidines and imidatesC. G. Saluste, S. Crumpler, M. Furber, R. J. Whitby*, Tetrahedron Lett., 2004, 45(38), 6995-6996

    PdCl2, dppftoluene, 220 h, 109 C, Cs2CO3 or NaOtBu

    3884%12 examples

    Br

    NH2tBuNC N

    HN tBu

    56271 Preparation of the conjugated polyene chains with the 1,4-dimethyl substitutionH.-S. Jeon, S. Koo*, Tetrahedron Lett., 2004, 45(38), 7023-7026

    n-BuLi, DBUTHF, benzene

    5292%4 examples

    Cl CO2Et

    CO2Et SO2Ph CO2Et

    CO2Et

    56272 Nitroalkanes and ethyl glyoxalate as common precursors for the preparation of both -keto esters and,-unsaturated estersR. Ballini*, D. Fiorini, A. Palmieri, Tetrahedron Lett., 2004, 45(38), 7027-7029

    MeSO2Cl, Amberlyst A-21Et3N, CH2Cl2, rt then 0 C, 1.5 h

    6594%12 examples

    H3CH2C NO2

    O

    OEtO

    H3CH2C

    NO2COOEt

    56273 -Addition of activated methylenes to alyknoates. A straightforward synthesis of multifunctionalcompoundsM. Hanedanian, O. Loreau, F. Taran*, C. Mioskowski*, Tetrahedron Lett., 2004, 45(38), 7035-7038

    PPh3AcOHAcONatoluene, 80110 C, up to 4h

    2388%11 examples

    COOEt

    O O

    COOEt

    OOH

    56274 Regioselective Pd-catalyzed alkylative lactonizations of 4-hydroxy-2-alkynecarboxylates withorganoboronic acidsC. H. Oh*, S. J. Park, J. H. Ryu, A. K. Gupta, Tetrahedron Lett., 2004, 45(38), 7039-7042

    AcOH, 1,4-dioxane, 80 C

    yield: 70%ee: 95%

    EtOOCEtOOC

    O

    PhB(OH)2EtOOCEtOOC

    O

    Pd(PPh3)4

    METHODS IN ORGANIC SYNTHESIS January 2005 35

  • Tetrahedron Letters

    56275 A novel glycosidation of glycosyl fluoride using a designed ionic liquid and its effect on thestereoselectivityK. Sasaki, S. Matsumura, K. Toshima*, Tetrahedron Lett., 2004, 45(38), 7043-7047

    protic acid, ionic liquid25 C, 14 h

    8289%6 examples

    OBnO

    BnO BnO F

    BnO

    HOOBnO

    BnO BnO O

    BnO

    56276 A convenient synthesis of 3-amino-4-imino(thioxo)-imidazolidin-2-onesT. Kurz*, K. Widyan, Tetrahedron Lett., 2004, 45(38), 7049-7051

    CDI or CDT & Et3N or THF, NaH, H2NNHC6H5

    5773%10 examples

    EtO PO

    EtONH

    CN EtO PO

    EtOHN

    N

    NH

    NH

    OC6H5

    56277 A two-step synthesis of aminopropylpiperidines via aminopropargylpyridines, suitable for the synthesisof a new class of 5-HT4 ligandsO. Russo, M. Alami*, J.-D. Brion, S. Sicsic, I. Berque-Bestel*, Tetrahedron Lett., 2004, 45(38), 7069-7072

    Et3N, DMF, 80 C, PdCl2(PPh3)2CuI

    5393%6 examples

    KN(Boc)2

    N Br Br+

    NNBoc2

    56278 The simple solvent-free synthesis of 1H-quinazoline-2,4-diones using supercritical carbon dioxide andcatalytic amount of baseT. Mizuno*, T. Wai, Y. Ishino, Tetrahedron Lett., 2004, 45(38), 7073-7075

    scCO2, 10 MPa, 80 C, 4 h

    4 examples5497%

    baseNH2

    CNNH

    HN

    O

    O

    56279 Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indolenatural product synthesisS. M. Allin*, C. I. Thomas, J. E. Allard, K. Doyle, M. R. J. Elsegood, Tetrahedron Lett., 2004, 45(38), 7103-7105

    rt, 20 h

    yield: 95%de 100%

    HCl, EtOH

    N

    O

    NHO

    H

    NH

    NH

    O

    HOH

    36 METHODS IN ORGANIC SYNTHESIS January 2005

  • Tetrahedron Letters

    56280 General facile synthesis of 2,5-diarylheteropentalenesP. Vachal*, L. M. Toth, Tetrahedron Lett., 2004, 45(38), 7157-7161

    Na2Co3, H2O, DMF, 2585 C, 23 h

    9 examples7491%

    PhI, Pd(Ph3P)4HS(HO)2B

    S

    Ph

    56281 Iodine-catalyzed synthesis of -keto enol estersR. S. Bhosale, S. V. Bhosale, S. V. Bhosale, T. Wang, P. K. Zubaidha*, Tetrahedron Lett., 2004, 45(39), 7187-7188

    I2, alcoholrt, 37 min

    O

    O

    O

    OMe

    9396%9 examples

    56282 Synthesis of -hydroxy nitriles and 1,3-amino alcohols from epoxides using acetone cyanohydrin as aLiCN precursorJ. A. Ciaccio*, M. Smrtka, W. A. Miao, D. Rucando, Tetrahedron Lett., 2004, 45(39), 7201-7204

    LiCNacetone0.253 h, THF

    6590%12 examples

    O OH

    (CH2)10CH3NC OH

    (CH2)10CH3

    HO

    56283 Catalysis of highly stereoselective Mannich-type reactions of ketones with -imino esters by apyrrolidine-sulfonamide. Synthesis of unnatural -amino acidsW. Wang*, J. Wang, H. Li, Tetrahedron Lett., 2004, 45(39), 7243-7246

    rt, DMSO, 220 h

    yield: 7491%ee: 9699%8 examples

    NH HN S

    O

    OCF3

    O+

    N

    HEtO2C

    PMP

    CO2Et

    O NHPMP

    56284 Enantioselective syntheses of bicyclo[3.1.0]hexane carboxylic acid derivatives by intramolecularcyclopropanationN. Yoshikawa*, L. Tan, N. Yasuda, R. P. Volante, R. D. Tillyer, Tetrahedron Lett., 2004, 45(39), 7261-7264

    3857%2 examples

    1. pyrrolidine, reflux2. TBSCl. imidazole, DMF, rt3. NMO, OsO4, acetoneH2O, rt4. SOCl2, Et3N, toluene, 0 C5. LiHMDS, THF, 78 C

    O

    H

    H

    HHHO

    HOTBS

    O

    N

    METHODS IN ORGANIC SYNTHESIS January 2005 37

  • Tetrahedron Letters

    56285 An efficient and green protocol for the preparation of cycloalkanols: a practical synthesis of venlafaxineS. P. Chavan*, D. A. Khobragade, S. K. Kamat, L. Sivadasan, K. Balakrishnan, T. Ravindranathan, M. K. Gurjar, U. R. Kalkote,Tetrahedron Lett., 2004, 45(39), 7291-7295

    5697%12 examples

    H2O, 45120 min, phase transfer catalysis

    NaOH or KOH

    OMe

    CN

    O

    +

    OMe

    CNOH

    56286 Synthesis of 1,2-dihydroisoquinolines via the reaction of ortho-alkynylarylamines with bis--allylpalladiumM. Ohtaka, H. Nakamura, Y. Yamamoto*, Tetrahedron Lett., 2004, 45(39), 7339-7341

    Cu(OAc)2, CH3CN, 50 C

    +

    NBn

    PhSnBu3

    Cl+

    PdCl

    PdCl

    N

    Ph

    Bn

    56287 A novel procedure for the synthesis of multifunctional ketones through the Fukuyama coupling reactionemploying dialkylzincsY. Mori, M. Seki*, Tetrahedron Lett., 2004, 45(39), 7343-7345

    ZnBr, THF, toluene, DMF, 20 C, 1748 h

    Et2Zn, Pd/C

    MeO

    O

    SEt

    O

    O

    Et

    5695%6 examples

    56288 Highly regioselective ring opening of epoxides using NaN3: a short and efficient synthesis of()-cytoxazoneJ. Boruwa, J. C. Borah, B. Kalita, N. C. Barua*, Tetrahedron Lett., 2004, 45(39), 7355-7358

    CH3CN, 1.01.6 h

    NaN3, 4 molecular sieves

    9097%9 examples

    O

    Cl N3 Cl

    OH

    56289 Bismuth trichloride catalyzed synthesis of -aminonitrilesS. K. De*, R. A. Gibbs, Tetrahedron Lett., 2004, 45(40), 7407-7408

    BiCl3, TMSCNCH3CN, rt, 510 h

    CHO + NH2 HN

    CN

    38 METHODS IN ORGANIC SYNTHESIS January 2005

  • Tetrahedron Letters

    56290 Synthesis of 4b,5,10a,11-tetrahydroindeno[1,2-b]-quinolin-10-ones from BaylisHillman adductsC. G. Lee, Y. Lee, S. GowriSankar, J. N. Kim*, Tetrahedron Lett., 2004, 45(40), 7409-7413

    PPA120170 C, 0.518 h

    NH HN

    O

    +

    N7 examples5062%

    5 examples422%

    56291 A simple, efficient, and highly selective method for the iodination of alcohols using ZrCl4/NaIH. Firouzabadi*, N. Iranpoor*, M. Jafarpour, Tetrahedron Lett., 2004, 45(40), 7451-7454

    ZrCl4/NaI2120 min, CH3CN

    14 examples7597%

    OH I

    56292 Curtius rearrangement and Wolff homologation of functionalized peroxidesP. H. Dussault*, C. Xu, Tetrahedron Lett., 2004, 45(40), 7455-7457

    EtOC(O)Cl then CH2N2

    11 examples4799%

    O OH

    t-BuO O

    O CHN2

    t-BuO O

    56293 Quinone methide initiated cyclization reaction: synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolinesB. C. Raju*, P. Neelakantan, U. T. Bhalerao*, Tetrahedron Lett., 2004, 45(40), 7487-7489

    3 examples7886%

    MeO

    MeONHTS

    +

    H3COBn

    CH3

    CH2Br

    H3COH

    CH3

    NTsHN

    OMe

    OMe

    1. NaH/DMF2. Pd/C, H23. Ag2O, DCM4. ZnCl2, DCM

    56294 Opening of epoxides with aromatic amines promoted by indium tribromide: a mild and efficient methodfor the synthesis of -amino alcoholsJ. R. Rodriguez, A. Navarro*, Tetrahedron Lett., 2004, 45(40), 7495-7498

    16 examples6596%

    +InBr3

    CH2Cl2, rtO

    7tBu NH2 7

    OHNH

    tBu

    56295 Synthesis and reactivity of enantiomerically pure N-alkyl-2-alkenyl azetidinium saltsF. Couty*, F. Durrat, G. Evano, D. Prim, Tetrahedron Lett., 2004, 45(40), 7525-7528

    7 examples6994%up to 72%

    KHMDS or PhLi

    N

    Ph

    Bn MeMe

    N

    Ph

    Me

    PhTfO

    Bn

    METHODS IN ORGANIC SYNTHESIS January 2005 39

  • Books, Reviews and Conference Proceedings

    Books, Reviews and Conference Proceedings

    56296 DNA-Templated organic synthesis: Natures strategy for controlling chemical reactivity applied tosynthetic moleculesX. Li, D. R. Liu*, Angew. Chem., Int. Ed., 2004, 43(37), 4848-4870

    A review, with 172 references, describing some representative early examples of nucleic acid templated synthesis,an analysis of current understanding of this technique, emerging applications and future challenges.

    56297 N-Heterocyclic carbenes: reagents, not just ligands!V. Nair*, S. Bindu, V. Sreekumar, Angew. Chem., Int. Ed., 2004, 43(39), 5130-5135

    A review, with 37 references, covering the use of N-heterocyclic carbenes as catalyst and nucleophilic reagents intransesterification, nucleophilic aromatic substitution, cycloaddition and asymmetric reactions.

    56298 In the golden age of organocatalysisP. I. Dalko*, L. Moisan, Angew. Chem., Int. Ed., 2004, 43(39), 5138-5175

    A review, with 251 references, covering the use of organic compounds as catalysts in a diverse range of reactions.

    56299 Stereoselective synthesis using diastereotopic groupsR. W. Hoffmann*, Synthesis, 2004, (13), 2075-2090

    A review, with 104 references, of stereoselective synthesis using diastereotopic group differentiating reactions,with conformationally flexible molecules.

    56300 Palladium catalysts for the Suzuki cross-coupling reaction: an overview of recent advancesF. Bellina, A. Carpita, R. Rossi*, Synthesis, 2004, (15), 2419-2440

    A review, with 206 references, of work until March 2004 on new catalyst systems for palladium catalysed Suzukicross-coupling rections of organic electrophiles and organoboron compounds.

    56301 Intermolecular CH insertions of donor/acceptor-substituted rhodium carbenoids: a practical solution forcatalytic enantioselective CH activationH. M. L. Davies*, O. Loe, Synthesis, 2004, (16), 2595-2608

    A review, with 58 references, covering recent developments in the rhodium-catalyzed intermolecular CHinsertion chemistry of diazo compounds.

    56302 Current methods for the synthesis of 2-substituted azolesC. A. Zificsak, D. J. Hlasta*, Tetrahedron, 2004, 60(41), 8991-9016

    A review, with 256 references, of recent literature focusing on new methods of substitution to construct CC bondsin preparing azole derivatives.

    56303 The Reformatsky reaction in organic synthesis. Recent advancesR. Ocampo, W. R. Dolbier, Jr.*, Tetrahedron, 2004, 60(42), 9325-9374

    A review, with 369 references, of the recent progress in the uses of Reformatsky reactions in synthetic organicchemistry. Included are recent work in diastereo- and enantioselective reactions.

    40 METHODS IN ORGANIC SYNTHESIS January 2005

  • Author Index

    Author Index

    Abe, H. 56191Abid, S. 56252Aikawa, K. 56186Alami, M. 56277Albert, M. 56151Albu, S. 56096Alcazar, E. 56199Alesi, S. 56107Alexakis, A. 56174Allard, J. E. 56279Allin, S. M. 56279Alonso, E. 56218Alper, H. 56171Alves, E. F. 56110Anderson, K. 56128Andersson, P. 56196Aubert, C. 56127Augustine, A. 56214Averina, E. B. 56213Azizian, J. 56203Bacque, E. 56182Balakrishnan, K. 56285Ballini, R. 56124, 56272Bandgar, B. P. 56229Banerjee, J. 56161Bao, H. 56230Barboni, L. 56124Barrett, A. G. M. 56163Barua, N. C. 56288Basak, A. K. 56227Bauer, T. 56263Beller, M. 56083, 56086Bellina, F. 56300Bennacer, B. 56179Bergmann, R. G. 56089,

    56090Berque-Bestel, I. 56277Bettigeri, S. V. 56229Bhalerao, U. T. 56293Bhor, S. 56086Bhosale, R. S. 56281Bhosale, S. V. 56281, 56281Biermann, U. 56134Bindu, S. 56297Blaszczyk, A. 56153Boas, U. 56207Bolm, C. 56157Bolourtchian, M. 56243Borah, J. C. 56288Boruwa, J. 56288Bosco, J. W. J. 56224Boto, A. 56194BouzBouz, S. 56169Bovin, Y. 56156Bowser, A. M. 56166Braga, A. L. 56110Brion, J.-D. 56277Bryliakov, K. P. 56085Buchwald, S. 56128Budynina, E. M. 56213Cadran, N. 56127Campbell, J. E. 56143Cao, W. 56257Cariou, K. 56127Carlo, G. 56124

    Carpita, A. 56300Carreira, E. 56198Carreno, M. 56175Castedo, L. 56133Chakraborti, A. K. 56262Chan, A. S. C. 56104Chan, K. S. 56104Chandraiah, L. 56208Chandrasekhar, S. 56108Chapman, C. 56196Chatani, N. 56180Chauhan, S. M. S. 56223Chavan, S. P. 56285Chavarot, M. 56103Che, C.-M. 56082Chen, F.-X. 56204Chen, J. 56082Chen, W. 56159Cho, G. Y. 56157Choi, K. I. 56239Choudary, B. 56126Christensen, J. B. 56207Ciaccio, J. A. 56282Ciufolini, M. A. 56156Colacot, T. 56189Colobert, F. 56175Corey, E. J. 56164, 56165Cossy, J. 56169, 56267Couty, F. 56295Cozzi, P. G. 56107Crumpler, S. 56270Cui, J. 56105Dalko, P. I. 56298Das, B. 56161, 56200,

    56237Das, S. K. 56258Davies, H. M. L. 56142,

    56301De, S. K. 56220, 56247,

    56289de Filippis, A. 56267Defieber, C. 56198del Pozo, C. 56218Delgado, A. 56133Delgado, F. 56219Deng, J. G. 56100Denmark, S. E. 56265Deprele, S. 56195Dey, S. 56225Di Blasio, B. 56242Diesen, J. 56196Ding, K. 56135Ding, W. 56257Dingerdissen, U. 56083Dobler, C. 56086Dolbier, W. R., Jr. 56303Dommisse, R. A. 56109Dong, C. 56171Dong, Y. 56211Doyle, K. 56279Duan, X.-F. 56240Dunach, E. 56244Durrat, F. 56295Dussault, P. H. 56292Early, T. R. 56098

    Ebitani, K. 56139Eeshwaraiah, B. 56235Ekstrand, M. 56106Ekthawatchai, S. 56172El Gharbi, R. 56252El Qacemi, M. 56182Elbing, M. 56153Elsegood, M. R. J. 56279Enthaler, S. 56083Evano, G. 56295Fabbri, D. 56188Feng, X. 56204Fensterbank, L. 56127Fernandez, S. 56192Ferrero, M. 56192Fery-Forgues, S. 56252Fiorentino, A. 56242Fiorini, D. 56272Firouzabadi, H. 56253,

    56291Fort, Y. 56209Frolich, R. 56183Fujii, T. 56173Fujioka, S. 56148Fujita, K. 56173Fujita, K.-i. 56092Fujiwara, M. 56179Funabiki, K. 56093Furber, M. 56270Gajare, A. S. 56119Gajewiak, J. 56263Garcia, J. 56192Garella, I. 56242Gentili, A. 56242Ghosh, R. 56152Gibbs, R. A. 56289Ging, D. 56241Giralt, E. 56121Giraud, I. 56245Giri, V. S. 56225Godet, T. 56156Gommermann, N. 56102Gondi, S. R. 56234Gonzalez, J. 56218Goodarzi, M. 56254Gotor, V. 56192Goushi, S. 56093GowriSankar, S. 56290Guo, H. 56233Gupta, A. 56168Gupta, A. K. 56274Gupta, M. K. 56101Gurjar, M. K. 56285Guy, I. L. 56097Ha, D.-C. 56261Habibi, M. H. 56222, 56255Hagemann, B. 56083Hallur, M. 56168Hampel, N. 56091Han, J. H. 56239Han, W. 56158Hancock, F. E. 56159Hanedanian, M. 56273Hara, T. 56139Harms, K. 56170

    Harrowven, D. C. 56097Hashimoto, S. 56193Haufe, G. 56183Hayashi, T. 56167Hazarkhani, H. 56253Hazell, R. G. 56096Hernandez, D. 56194Hernandez, R. 56194Herrera, A. 56246Herve, G. 56127Hirao, T. 56210Hlasta, D. J. 56302Hoffmann, M. 56091Hoffmann, R. W. 56299Hoge, G. 56181Holmes, A. B. 56098Hong, B. 56168Hosseini, M. 56243Hoveyda, A. 56140Hoveyda, A. H. 56143Hu, J. 56084, 56114Hu, X. 56178Hu, Y. 56251Hua, Z. 56155Huang, C.-H. 56240Huang, S. 56238Hugl, H. 56086Hurtshouse, M. B. 56269Ichikawa, E. 56151Ikagawa, A. 56145Ikariya, T. 56145Imagawa, H. 56184Iranpoor, N. 56221, 56253,

    56291Ishino, Y. 56278Ishizuka, T. 56193Islam, S. 56228Itami, K. 56185Ivanova, O. A. 56213Iwai, K. 56260Jafarpour, M. 56291Jagadeesh, B. 56101Jain, N. 56223Jaisankar, P. 56225Jansson, J. 56157Jantos, K. 56170Jasoni, R. L. 56114Jeon, H.-S. 56271Jiao, N. 56115Jin, Q. 56142Jin, T. 56112Jin, T.-S. 56232Jin, Z. 56155Johannesen, S. A. 56096Johnson, J. S. 56120Junge, K. 56083Kacprzynski, M. 56140Kakiuchi, F. 56180Kalita, B. 56288Kalkote, U. R. 56285Kamat, S. K. 56285Kambe, N. 56160Kamijo, S. 56112Kamounah, F. S. 56207Kanai, M. 56151

    METHODS IN ORGANIC SYNTHESIS January