Efficient asymmetric synthesis of 2,3-diamino-3-phenylpropanoic acid derivatives

被引：49

作者：

Lee, SH

Yoon, J ^{[1
]}

Chung, SH

Lee, YS

机构：

[1] Silla Univ, Dept New Mat Chem, Pusan 617736, South Korea

[2] Seoul Natl Univ, Sch Chem Engn, Seoul 151742, South Korea

来源：

TETRAHEDRON | 2001年 / 57卷 / 11期

基金：

新加坡国家研究基金会;

关键词：

2,3-diamino-3-phenylpropanoic acid derivatives; isopropyl cinnamate; catalytic hydrogenation;

D O I：

10.1016/S0040-4020(01)00090-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, stereoselective synthesis of selectively-protected anti and syn, methyl 2-amino-3-Boc-amino)-3-phenylpropanoate is described. Preparation of syn beta -acetylamino-alpha -hydroxy ester was from isopropyl cinnamate via an acetamide-based Sharpless aminohydroxylation (AA), and its anti isomer was obtained via C-alpha epimerization of the syn isomer. For the installation of a second amino group, two different approaches, involving substitution of the beta -hydroxyl group with azide, were investigated. The first was a ring-opening reaction of trans-oxazoline-5-carboxylate with trimethylsilyl azide, which produced anti beta-(acetylamino)-alpha -azido esters, which then transformed into the anti isomer; whereas the cis-oxazoline-5-carboxylate was found to be unreactive under this reaction condition. The second approach used the Mitsunobu reaction of syn and anti beta-(Boc-amino)-alpha -hydroxy esters with hydrazoic acid, followed by catalytic hydrogenation, which gave both anti and syn isomers, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2139 / 2145

页数：7

共 30 条

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