Factors affecting the efficiency and stereoselectivity of α-amino acid synthesis by the Petasis reaction

被引：52

作者：

Southwood, TJ

Curry, MC

Hutton, CA ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

[2] Univ Melbourne, Sch Chem, Melbourne, Vic 3010, Australia

[3] Univ Melbourne, Mol Sci & Biotechnol Inst Bio21, Melbourne, Vic 3010, Australia

来源：

TETRAHEDRON | 2006年 / 62卷 / 01期

基金：

澳大利亚研究理事会;

关键词：

amino acids; Petasis reaction; multi-component coupling; boronic acid Mannich reaction;

D O I：

10.1016/j.tet.2005.09.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of chiral secondary amines containing only one branched substituent has been shown to give optimal yields and stereoselectivities in the preparation of alpha-amino acids using the Petasis reaction. While the use of chiral primary amines generally gives products in low to moderate diastereoselectivity, chiral secondary amines generally give products in >95:5 diastereoselectivity. Additionally, the use of amines with two chiral (and by definition, branched) N-alkyl substituents results in significantly reduced yields with respect to to secondary amines with one or no branched N-alkyl substituents. (c) 2005 Elsevier Ltd. All rights reserved.

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收藏

页码：236 / 242

页数：7

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