A highly enantioselective one-pot sulfur ylide epoxidation reaction

A highly enantioselective one-pot sulfur ylide epoxidation reaction

Enantiomerically pure tricyclic C 2-symmetric sulfide 1 can be prepared in high yield and only three steps from d-mannitol. When used in a one-pot sulfur ylide mediated epoxidation reaction, between 94 and 98% enantiomeric excess was obtained; the highest reported to date for the catalytic process....

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Bibliographic Details
Published in:Tetrahedron letters Vol. 43; no. 31; pp. 5427 - 5430
Main Authors: Winn, Caroline L., Bellenie, Benjamin R., Goodman, Jonathan M.
Format: Journal Article
Language:English
Published: Elsevier Ltd 29-07-2002
Online Access:Get full text
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Summary:Enantiomerically pure tricyclic C 2-symmetric sulfide 1 can be prepared in high yield and only three steps from d-mannitol. When used in a one-pot sulfur ylide mediated epoxidation reaction, between 94 and 98% enantiomeric excess was obtained; the highest reported to date for the catalytic process. Molecular modelling studies of the ylide conformation provides a basis for understanding the stereochemical outcome of the reaction. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01072-9