Aziridine-mediated asymmetric synthesis of quaternary β-amino acids using 2H-azirine 2-carboxylate esters

被引：49

作者：

Davis, FA ^{[1
]}

Deng, JH

Zhang, YL

Haltiwanger, RC

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] GlaxoSmithKline, King Of Prussia, PA 19406 USA

来源：

TETRAHEDRON | 2002年 / 58卷 / 35期

基金：

美国国家卫生研究院;

关键词：

asymmetric synthesis; aziridines; beta-amino acids; N-sulfinyl imines;

D O I：

10.1016/S0040-4020(02)00727-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective hydrogenation of enantiopure 3-substituted and 3,3-disubstituted aziridine 2-carboxylate esters affords beta-amino acids and quaternary beta-amino acids, respectively, in good yield. The aziridines are prepared via an aza-Darzens reaction of alpha-bromoenolates with enantiopure sulfinimines (N-sulfinyl imines) and by addition of Grignard reagents to 2H-azirine 2-carboxylate esters. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：7135 / 7143

页数：9

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