Copper(II)salen catalysed, asymmetric synthesis of α,α-disubstituted amino acids

被引：51

作者：

Belokon, YN

Bhave, D

D'Addario, D

Groaz, E

North, M ^{[1
]}

Tagliazucca, V

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 | 2004年 / 60卷 / 08期

关键词：

Cu(salen) complex; phase transfer methodology; alkylation;

D O I：

10.1016/j.tet.2003.12.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cu(salen) complex 1 was found to be a versatile catalyst for the asymmetric alkylation of a range of enolates derived from a-amino acids, leading to alpha,alpha-disubstituted amino acids. The enantioselectivity of the process decreases as the size of the amino acid sidechain increases, but functionalized amino acids such as allylglycine and aspartic acid are substrates for the process. Benzylic bromides are found to be more enantioselective alkylating agents than propargylic bromides. As an example of the utility of this chemistry, an a-propargylic allylglycine derivative is prepared and subjected to ene-yne metathesis using Grubbs' catalyst to give a non-racemic cyclopentenyl amino acid. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：1849 / 1861

页数：13

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