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
收藏
页码：5427 / 5430
页数：4
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