Synthesis of enantiomerically enriched β,γ-unsaturated-α-amino acids

被引：32

作者：

Rose, NGW ^{[1
]}

Blaskovich, MA ^{[1
]}

Wong, A ^{[1
]}

Lajoie, GA ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

TETRAHEDRON | 2001年 / 57卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

vinylglycines; olefination; alpha-amino acid;

D O I：

10.1016/S0040-4020(00)01146-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of enantiomerically enriched beta,gamma -unsaturated-alpha -amino acids are synthesized by olefination of a Cbz-protected serine aldehyde equivalent, readily prepared from serine. A cyclic ortho ester protecting group is employed to minimize racemization. The deprotected amino acids are obtained in good yield, ranging from 70-95% ee, with double-bond geometry determined by the type of Wittig reagent used. Isotopically labeled side chains are readily introduced by this procedure, and free gamma-C-13-vinylglycine was prepared in 44% yield from the protected serine aldehyde synthon. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1497 / 1507

页数：11

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