ChemInform Abstract: Lewis Acid Stereocontrolled Addition of a Silyl Ketene Acetal to...
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2001 nucleic acids nucleic acids U 0700 08 - 216 Lewis Acid Stereocontrolled Addition of a Silyl Ketene Acetal to 2,3-Di-O-isopropylidene-D-glyceraldehyde Nitrones. Synthesis of L-Isoxazolidinyl Nucleosides. — Under optimized conditions, the BF 3 - etherate promoted addition of the silyl ketene acetal (II) to a D-glyceraldehyde derived nitrone (I) gives the isoxazolidinone (III) in high yield and stereoselectiv- ity. The anti product is readily converted to key intermediates (VIII) and (IX) of L-isoxazolidinyl nucleosides such as (X) and (XI). — (MERINO, PEDRO; DEL ALAMO, EVA M.; BONA, MAITE; FRANCO, SANTIAGO; MERCHAN, FRANCISCO L.; TEJERO, TOMAS; VIECELI, ODILE; Tetrahedron Lett. 41 (2000) 48, 9239-9243; Dep. Quim. Org., ICMA, Fac. Cienc., Univ. Zaragoza, Aragon, E-50009 Zaragoza, Spain; EN) 1
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Transcript of ChemInform Abstract: Lewis Acid Stereocontrolled Addition of a Silyl Ketene Acetal to...
2001 nucleic acids
nucleic acidsU 0700
08 - 216Lewis Acid Stereocontrolled Addition of a Silyl Ketene Acetal to2,3-Di-O-isopropylidene-D-glyceraldehyde Nitrones. Synthesis ofL-Isoxazolidinyl Nucleosides. — Under optimized conditions, the BF3-etherate promoted addition of the silyl ketene acetal (II) to a D-glyceraldehydederived nitrone (I) gives the isoxazolidinone (III) in high yield and stereoselectiv-ity. The anti product is readily converted to key intermediates (VIII) and (IX)of L-isoxazolidinyl nucleosides such as (X) and (XI). — (MERINO, PEDRO;DEL ALAMO, EVA M.; BONA, MAITE; FRANCO, SANTIAGO; MERCHAN,FRANCISCO L.; TEJERO, TOMAS; VIECELI, ODILE; Tetrahedron Lett. 41(2000) 48, 9239-9243; Dep. Quim. Org., ICMA, Fac. Cienc., Univ. Zaragoza,Aragon, E-50009 Zaragoza, Spain; EN)
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