SYNTHESIS OF CYCLIC AMINES AND ALLYLIC SULFIDES BY PHENYLTHIO MIGRATION OF BETA-HYDROXY SULFIDES

被引：25

作者：

COLDHAM, I ^{[1
]}

WARREN, S ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 14期

关键词：

D O I：

10.1039/p19930001637

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rearrangement of beta-hydroxy sulfides proceeds stereospecifically with capture of the episulfonium ion by the nitrogen atom of an amide. Almost quantitative yields of substituted pyrrolidines are obtained using a sulfonamide as the intramolecular nucleophile and with activation by trimethylsilyl trifluoromethanesulfonate (TMSOTf). With a free amine no cyclization takes place, but instead allylic sulfides are formed.

引用

页码：1637 / 1656

页数：20

共 34 条

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