A highly enantioselective one-pot sulfur ylide epoxidation reaction

被引：46

作者：

Winn, CL ^{[1
]}

Bellenie, BR ^{[1
]}

Goodman, JM ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 31期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(02)01072-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure tricyclic C-symmetric sulfide I 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. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5427 / 5430

页数：4

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