RING-OPENING OF N-TOSYL AZIRIDINES BY 2-LITHIODITHIANES

被引：11

作者：

HOWSON, W

OSBORN, HMI

SWEENEY, J

机构：

[1] UNIV BRISTOL, SCH CHEM, BRISTOL BS8 1TS, AVON, ENGLAND

[2] PARKE DAVIS NEUROSCI RES CTR, CAMBRIDGE CB2 2QB, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 19期

关键词：

D O I：

10.1039/p19950002439

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of lithiated dithianes 6-8 and 15 and 16 with enantiopure N-sulfonylated aziridines; 1 and 2 leads via regiospecific nucleophilic ring-opening to enantiopure N-tosyl 2-(2'-dithianyl) secondary amines in good to. excellent yields. These compounds may be either desulfonylated or hydrolytically desulfurized to give the corresponding amines 21-24 or carbonyl compounds 25-27 and 28-30 in good yield. In the case of alpha-silaalkanones 31 and 32 produced by these reactions, oxidation furnishes enantiopure 3-tosylamino acids 33 and 34 in good yield.

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页码：2439 / 2445

页数：7

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