Asymmetric synthesis of β,γ-unsaturated α-amino acids via efficient kinetic resolution with cinchona alkaloids

被引：14

作者：

Hang, Jianfeng ^{[1
]}

Deng, Li ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02454 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 14期

关键词：

beta; gamma-Unsaturated alpha-amino acids; Modified cinchona alkaloids; Asymmetric synthesis; Catalysis; Kinetic resolution; Dynamic kinetic resolution; L-VINYLGLYCINE; ENANTIOSELECTIVE SYNTHESIS; STRECKER REACTION; STEREOSELECTIVE-SYNTHESIS; DEHYDROAMINO ACIDS; VINYL GLYCINES; DERIVATIVES; (E)-VINYLGLYCINES; REARRANGEMENT; CATALYSIS;

D O I：

10.1016/j.bmcl.2009.03.152

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The beta,gamma-unsaturated amino acids are versatile chiral building blocks and biologically interesting compounds. The asymmetric synthesis of beta,gamma-unsaturated amino acids presents a challenging task as these compounds are labile toward racemization as well as the undesirable double bond isomerization. An efficient, general and mild kinetic resolution with readily accessible and fully recyclable cinchona alkaloid catalysts has been developed to provide a reliably useful approach toward optically active beta,gamma-unsaturated amino acids. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3856 / 3858

页数：3

共 47 条

[11] REACTIONS OF AN ELECTROPHILIC GLYCINE CATION EQUIVALENT WITH GRIGNARD-REAGENTS - A SIMPLE SYNTHESIS OF BETA,GAMMA-UNSATURATED AMINO-ACIDS [J].