Career Summary - Home - Department of Chemistry Summary Xiaopeng Yin The Wulff Group Michigan State...
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Career Summary
Xiaopeng Yin The Wulff Group
Michigan State University 6/6/2014
Eric N. Jacobsen
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About Eric N. Jacobsen
PERSONAL Born February 22, 1960, New York, N.Y. Married to Virginia Estevez on May 17, 1997. Three daughters (Adriana, Isabel, and Emilia) EDUCATION 1978-1982: New York University, New York, New York.
Degree awarded: B.S. in Chemistry Research advisor (1981-1982): Professor Yorke E. Rhodes
1982-1986: University of California, Berkeley, California. Degree awarded: Ph.D. Research advisor: Professor Robert G. Bergman
1986-1988: National Institutes of Health Postdoctoral Fellow Massachusetts Institute of Technology, Cambridge, Massachusetts. Research advisor: Professor K. Barry Sharpless Development of the osmium-catalyzed asymmetric dihydroxylation reaction.
EMPLOYMENT 1988-1993: University of Illinois at Urbana-Champaign
Assistant Professor (June 1988-September 1991) Associate Professor (September 1991-June 1993)
1993-present: Harvard University Professor (July 1993-June 2001) Sheldon Emery Professor of Chemistry (July 2001-present)
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Group Members Present Graduate Students: 9 Postdocs: 11 Past Ph.D Students: 37 Postdocs: 80
Mini Group Reunion in summer 2011
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Publications
1983-2014 186 research articles (70 JACS, 27 Angew, 2 Science, 1 Nature, 1 Natrue Chem.) 23 reviews 16 patents
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Citations
Sum of Times Cited without self-citations : 28014 Citing Articles without self- citations: 15081 Average Citations per Item: 158.21
Top 3 cited research articles: 1. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. "Enantioselective Epoxidation of
Unfunctionalized Olefins Catalyzed by (salen)Manganese Complexes," J. Am. Chem. Soc. 1990, 112, 2801–2803 (1243, 50/y)
2. Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. "Asymmetric Catalysis with Water: Efficient Kinetic Resolution of Terminal Epoxides by Means of Catalytic Hydrolysis," Science 1997, 277, 936–938. (900, 50/y)
3. Schaus, S. E.; Brandes, B. D; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. "Highly Selective Hydrolytic Kinetic Resolution of Terminal Epoxides Catalyzed by Chiral (salen)Cobalt(III)-Complexes. Practical Synthesis of Enantioenriched Terminal Epoxides and 1,2-Diols," J. Am. Chem. Soc. 2002, 124, 1307–1315. (616, 47/y)
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Catalysts*
79
39
16 17
Salen Complexes H-bond Donors (Schiff Base)Cr Complex Other
* Summarized from 151 Independent research papers in selected journals
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Metal of Salen Complexes *
26
23
16
11 3
Co Mn Cr Al Cu
* Summarized from 151 Independent research papers in selected journals
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H-bond Donors*
32
4 3
thiourea urea guanidinium
* Summarized from 151 Independent research papers in selected journals
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Reaction*
20
31
4
10 10 7 6
23
5
8 7 12 8
Epoxidation Epoxides Ring Opening Aziridinization Conjugate Addition Cycloadditions C=C functionalization C=O functionalization C=N functionalization C=O α-functionalization Mechanism Study Catalyst Study Total Synthesis other
* Summarized from 151 Independent research papers in selected journals
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Jacobsen Asymmetric Epoxidation of Olefins
Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801–2803 Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063–7064
9 substrates, 36-75% yield, 20-93% ee, only cis-alkene gave good results
6 cis-alkene substrates, 63-96% yield, 89-98% ee
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Preparation of Catalyst
Palucki, M.; Finney, N.S.; Pospisil, P.J.; Güler, M.L.; Ishida, T.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, 948–954
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“Side on” Mechanism
Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063–7064 Palucki, M.; Finney, N.S.; Pospisil, P.J.; Güler, M.L.; Ishida, T.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, 948–954
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Substrate limitation
Properties favoring high enantioselectivity
Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martínez, L. E. Tetrahedron 1994, 50, 4323–4334 Palucki, M.; Pospisil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333–9334
Terminal alkenes
mCPBA, -78°C, 30 min, Catalyst 3 88% yield, 86% ee
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Substrate limitation
Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378–4380 Brandes, B. D.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5123–5126
Trisubstituted alkenes
6 substrates, 61-97% yield, 86-95% ee,
Tetrasubstituted alkenes
Catalyst 2, 84% yield, 96% ee Catalyst 2, 81% yield, 97% ee
Catalyst 3, 45% yield, 65% ee Catalyst 3, 37% yield, 35% ee
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Trans Epoxides
Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425–426 Chang, S.; Lee, N. H.; Jacobsen, E. N. J. Org. Chem. 1993, 58, 6939–6941 Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937–6938
65% yield, t/c = 5:1 98% ee 58% yield, t/c = 7:1 83% ee 81% yield, t/c = 9:1 87% ee
Cis-enynes and cis-dienes
Chiral Quaternary Ammonium Salts additives
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Ring Opening of Epoxides
Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897–5898
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Kinetic Resolution with TMSN3
Larrow, J.F.; Schaus, S.E.; Jacobsen, E.N. J. Am. Chem. Soc. 1996, 118, 7420–7421
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Hydrolytic Kinetic Resolution (HKR)
Tokunaga, M.; Larrow, J.F.; Kakiuchi, F.; Jacobsen, E.N. Science 1997, 277, 936–938
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Mechanism and Improvement
Nielsen, L. C. P.; Stevenson, C. P.; Blackmond, D.G.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 1360–1362 Nielsen, L. P. C.; Zuend, S. J.; Ford, D. D.; Jacobsen, E. N. J. Org. Chem., 2012, 77, 2486–2495
Method A: X = OAc Method B: X = OTs
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Mechanism and Improvement
Ready, J. R.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 41, 1374–1377. Breinbauer, R.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2000, 39, 3604–3607
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Stereochemical Communication Between Catalysts
Ford, D. D.; Nielsen, L. P. C.; Zuend, S. J.; Musgrave, C. B.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 15595–15608
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Phenolytic Kinetic Resolution (PKR)
Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086–6087
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Asymmetric Alkene Aziridination
Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326–5327 Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889–5890
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Enantioselective Michael Additions
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Enantioselective Michael Additions
Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959–8960 Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442–4443
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Enantioselective Michael Additions
Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928–9929
Cooperative Dual Catalysis
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Enantioselective Michael Additions
Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204–11205
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Enantioselective Michael Additions
Taylor, M. S.; Zalatan, D. N.; Lerchner, A. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 1313–1317
9 examples, 76-93% yield, 75-96% ee,
8 examples, 70-90% yield, 88-95% ee,
7 examples, 72-97% yield, 61-94% ee,
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Asymmetric Hetero-Diels-Alder Reactions
Schaus, S.E.; Brånalt, J.E.; Jacobsen, E.N. J. Org. Chem. 1998, 63, 403–405
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Asymmetric Hetero-Diels-Alder Reactions
Dossetter, A. G.; Jamison, T. F.; Jacobsen, E. N. "Angew. Chem. Int. Ed. 1999, 38, 2398–2400
14 examples, 50-97% yield, 81-99% ee,
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Total Synthesis of FR901464
Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2000, 122, 10482–10483 Thompson, C. F.; Jamison, T. F.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 9974–9983.
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Total Synthesis of (+)-Ambruticin
Liu, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 10772–10773
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Synthesis of the Catalyst
Schaus, S.E.; Brånalt, J.E.; Jacobsen, E.N. J. Org. Chem. 1998, 63, 403–405
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Inverse Electron Demand Hetero-Diels–Alder Reactions
Gademann, K.; Chavez, D. E.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2002, 41, 3059–3061 Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563–2565
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Quinone Diels–Alder Reactions and Application
Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44, 6043–6046 Boezio, A. A.; Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44, 6046–6050
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Hetero-Ene Reactions
Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882–2883 Ruck, R. T.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2003, 42, 4771–4774 Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1469–1472
18 examples, 50-98% yield, 70-96% ee
6 examples, 47-90% yield, 87-93% ee
42% yield, 93% ee, dr>30:1
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Asymmetric Strecker Reaction
Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, 5315–5316 Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, 4901–4902
R= Ar, 7 examples, 91-99 % yield, 79-95% ee R= Alkyl, 2 examples, 69-77 % yield, 37-57% ee
M = Al(III)Cl
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Thiourea Catalyst
Sigman, M.S.; Jacobsen, E.N. J. Am. Chem. Soc. 1998, 120, 4901–4902
6 examples, 65-92 % yield, 70-91% ee
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Mode of Activation
Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012–10014
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Mode of Activation
Zuend, S. J.; Coughlin, M. P.; Lalonde, M. P.; Jacobsen, E. N. Nature 2009, 461, 968–970 Zuend, S. J., Jacobsen, E. N. J. Am. Chem. Soc. 2009, 131, 15358–15374
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Activation of Imines
Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964–12965 Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102–4103
R= Ar, 14 examples, 84-99 % yield, 86-98% ee
Hydrophosphonylation
18 examples, 52-93 % yield, 81-99% ee
Mannich Reactions
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Activation of Imines and Ketones
Xu, H.; Zuend, S. J.; Woll, M. P.; Tao, Y.; Jacobsen, E. N. Science 2010, 327, 986–990 Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964–8965
Cyanosilylation of Ketones
18 examples, 81-98 % yield, 86-98% ee
Povarov Reactions
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H-bonding Anion Stabilization
Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558–10559 Brown, A. R.; Uyeda, C.; Raheem, I. T.; Thiara, P. V.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404–13405
Acyl-Pictet-Spengler Reactions
Pictet-Spengler-Type Cyclizations
7 examples, 65-81 % yield, 85-95% ee
15 examples, 51-94 % yield, 81-99% ee
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H-bonding Anion Stabilization
Raheem, I. T.; Thiara, P. V.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404–13405
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H-bonding Anion Stabilization
Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198–7199
Additions to Oxocarbenium Ions
6 examples, 71-96 % yield, 74-90% ee
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H-bonding Anion Stabilization
Knowles, R. R.; Lin, S.: Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030–5032 Veitch, G. E.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2010, 49, 7332–7335
Cationic Polycyclizations
Iodolactonization
9 examples, 71-96 % yield, 48-96% ee
7 examples, 51-77 % yield, 89-94% ee
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H-bonding Anion Stabilization
Brown, A. R.; Kuo, H.-S.; Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 9286–9288 Burns, N. Z.; Witten, M. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2011, 133, 14578–14581
α-Alkylation of Aldehydes
9 examples, 52-770% yield, 85-94% ee
[5+2] Pyrylium Cycloadditions
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H-bonding TS Stabilization
Uyeda, C.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 9228–9229 Brown, A. R.; Uyeda, C.; Brotherton, C. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2013, 135, 6747–6749
Guanidinium Catalysts
Claisen Rearrangements
Cope-Type Hydroamination
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