InCl3-catalyzed regio- and stereloselective thiolysis of α,β-epoxycarboxylic acids in water

被引：63

作者：

Fringuelli, F ^{[1
]}

Pizzo, F ^{[1
]}

Tortoioli, S ^{[1
]}

Vaccaro, L ^{[1
]}

机构：

[1] Univ Perugia, CEMIN, Dipartimento Chim, I-60123 Perugia, Italy

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 20期

关键词：

D O I：

10.1021/ol051582y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The thiolysis of alpha,beta-epoxycarboxylic acids la-e by thiois 2a,b is more efficient in water than in dichloromethane or SFC. At pH 9.0 phenylthiolate generally attacks the C-alpha carbon while at pH 4.0, and in the presence of InCl3 (10 mol %), the thiolysis is exclusively C-beta regioselective. In all cases, the processes are completely anti-diasteroselective, and the corresponding products 3, 4, and 5 have been isolated in good yields. Both water and catalysts have been recovered and reused.

引用

页码：4411 / 4414

页数：4

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