Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

被引：32

作者：

Karoyan, P ^{[1
]}

Chassaing, G ^{[1
]}

机构：

[1] UNIV PARIS 06,CNRS,LAB CHIM ORGAN BIOL,F-75252 PARIS 05,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(97)00203-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reacted with S-methyl methanesulfonothioate leading in a ''one-pot'' procedure, to N-(alpha-methylbenzyl)-3-prolinomethionine benzyl ester. The alpha-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyloxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer. (C) 1997 Elsevier Science Ltd.

引用

页码：2025 / 2032

页数：8