Catalytic, asymmetric synthesis of α,α-disubstituted amino acids

被引：30

作者：

Belokon', YN

Bhave, D

D'Addario, D

Groaz, E

Maleev, V

North, M

Pertrosyan, A

机构：

[1] Kings Coll London, Dept Chem, London WC2R 2LS, England

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 10期

基金：

俄罗斯基础研究基金会;

关键词：

alpha; alpha-disubstituted amino acid; enolate alkylation; asymmetric catalysis; copper(salen) complex;

D O I：

10.1016/S0040-4039(03)00170-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(salen) complex 1 has been found to catalyse the asymmetric alkylation of enolates derived from a variety of amino acids. There is a clear relationship between the size of the side chain in the substrate and the enantioselectivity of the process, so that the enantioselectivity decreases in the order alanine>aminobutyric acid>allylglycine>leucine>phenylalanine> valine. A transition state model which accounts for the influence of the size of the side chain on the enantioselectivity of the reactions is presented. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：2045 / 2048

页数：4

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