(S)-dimethylsulfonium(p-tolysulfinyl)methylide:: A new chiral sulfonium ylide and its use in asymmetric epoxidation

被引：12

作者：

Midura, WH ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, PL-90363 Lodz, Poland

来源：

SYNLETT | 2006年 / 05期

关键词：

asymmetric synthesis; chiral auxiliaries; ylides; epoxidation; sulfoxides;

D O I：

10.1055/s-2006-933131

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The title optically active sulfonium ylide was prepared by methylation of easily available (-)-(S)-p-tolymethylthiomethylsulfoxide and subsequent deprotonation. Its reaction with aldehydes gave alpha,beta-epoxy sulfoxides with full enantioselectivity and moderate diastereoselectivity. The steric course of acid-catalyzed rearrangement of sulfinyl oxiranes is briefly discussed.

引用

页码：733 / 736

页数：4

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