A general asymmetric synthesis of syn- and anti-β-substituted cysteine and serine derivatives

被引：48

作者：

Xiong, CY ^{[1
]}

Wang, W ^{[1
]}

Hruby, VJ ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 10期

关键词：

D O I：

10.1021/jo011172x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereodivergent synthetic route has been developed to make the optically pure anti- and syn-beta-substituted cysteine and serine derivatives. In this approach, the key intermediates, >94% enantiomerically pure cyclic sulfates 3 and aziridines 7, were prepared from alpha,beta-unsaturated esters 1, employing the Sharpless asymmetric dihydroxylation. The high regio- and stereoselective ning-opening reactions of cyclic sulfates and aziridines provided enantiomerically pure beta-substituted cysteine and serine derivatives.

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页码：3514 / 3517

页数：4

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