Activation of oxaziridines by Lewis acids:: Application in enantioselective sulfoxidation

被引：42

作者：

Schoumacker, S

Hamelin, O

Téti, S

Pécaut, J

Fontecave, M

机构：

[1] Univ Grenoble 1, CEA,CNRS, Lab Chim & Biochim,Ctr Redox Biol,DRDC CB, UMR 5047, F-38054 Grenoble, France

[2] CEA, DRFMC, F-38054 Grenoble, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 01期

关键词：

D O I：

10.1021/jo048380k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of new and easily accessible chiral N-alkyloxaziridines for asymmetric sulfides oxidation was investigated. Most significantly, we report here that inert N-alkyloxaziridines can be activated by Lewis acids to achieve a fast, selective, and efficient oxygen atom transfer to sulfides. Asymmetric sulfoxidation by three new chiral oxaziridines (two of them were structurally characterized by X-ray analysis) afforded enantioselectivities ranging from 22% to 63% ee with the simplest aryl alkyl sulfides.

引用

页码：301 / 308

页数：8

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