Enantioselective synthesis of aroylalanine derivatives

被引:30
作者
Lygo, B [1 ]
Andrews, BI [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(03)01017-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this paper we report the development of a highly enantioselective method for the synthesis of aroylalanines. The approach described employs a protected 2-amino-4-bromopent-4-enoic acid, generated via the asymmetric phase-transfer catalyzed alkylation of a glycine imine, as a key intermediate. Suzuki coupling with an aryl boronic acid followed by ozonolysis of the resulting styrene provides efficient access to the aroylalanine derivatives. The utility of this methodology is illustrated by the synthesis Of L-kynurenine along with several aroylalanine inhibitors of the kynurenine pathway. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4499 / 4502
页数:4
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