LEWIS ACID-INDUCED REARRANGEMENT OF 2,3-EPOXY SULFIDES - REGIOSPECIFIC NUCLEOPHILIC TRAPPING OF THIIRANIUM ION INTERMEDIATES WITH NITROGEN NUCLEOPHILES

被引：18

作者：

GILL, DM

PEGG, NA

RAYNER, CM

机构：

[1] UNIV LEEDS,SCH CHEM,LEEDS LS2 9JT,W YORKSHIRE,ENGLAND

[2] GLAXO GRP RES LTD,WARE SG12 0DP,HERTS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 13期

关键词：

D O I：

10.1039/p19930001371

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis acid-induced isomerisation of 2,3-epoxy sulfides into the corresponding 3-trimethylsilyloxy-1,2-thiiranium ions is described. Such intermediates react with nitrogen nucleophiles regiospecifically to form 1-substituted 3-hydroxy 2-thioethers in good to moderate yields with full stereochemical control.

引用

页码：1371 / 1372

页数：2

共 26 条

[1] TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS [J].