Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A

被引：69

作者：

Armstrong, A ^{[1
]}

Scutt, JN ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 13期

关键词：

D O I：

10.1021/ol0346887

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Herein we report a concise synthesis of 3-(trans-2-aminacyclopropyl)alanine, a component of belactosin A, using asymmetric alkylation of a glycine enolate in the presence of chiral phase-transfer catalysts to control the configuration at C2. Reaction of protected glycidol with triethyl phosphonoacetate (Wadsworth-Emmons cyclopropanation) is used for enantiospecific preparation of an intermediate cyclopropanecarboxylate that is converted to a cyclopropylamine via Curtius rearrangement.

引用

页码：2331 / 2334

页数：4

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