Novel stereoselective sulfur ylide epoxidation reaction catalyzed by ferrocenylsulfide

被引：0

作者：

汪磊

黄志真

机构：

[1] Department of Chemistry Zhejiang University

[2] China

[3] Department of Chemistry Zhejiang University Hangzhou 310027

来源：

Journal of Zhejiang University Science A(Science in Engineering) | 2005年 / 07期

基金：

中国国家自然科学基金;

关键词：

Ferrocenylsulfide; Catalytic ylide epoxidation; Stereoselectivity;

D O I：

暂无

中图分类号：

O643.3 [催化];

学科分类号：

081705 ;

摘要：

A range of ferrocenyl sulfides are synthesized and screened. Among them 1-α-methysulphoferrocenyl ethyl acetate and 1-α-methysulphoferrocenyl alcohol are found to be unexpected catalysts, which is first reported mediating in sulfur ylide epoxidation reactions, furnishing a novel approach for highly stereoselective synthesis of oxiranes with 98%-100% trans-isomer. The protocol also has excellent yield, convenient workup and recycled starting material. The reason of high trars-selectivity is due to the bulky ferrocenyl sulfide group, which stabilizes the intermediates and determines the trans priority. A possible catalytic mechanism is also proposed.

引用

页码：636 / 639

页数：4