Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

被引：44

作者：

Barfoot, CW

Harvey, JE

Kenworthy, MN

Kilburn, JP

Ahmed, M

Taylor, RJK ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] GlaxoSmithKline, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON | 2005年 / 61卷 / 13期

基金：

英国生物技术与生命科学研究理事会;

关键词：

cross-coupling; alpha-amino acids; organolithium; Suzuki; alanine anions;

D O I：

10.1016/j.tet.2004.10.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Homochiral, highly functionalised organolithium reagents derived from L-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through beta-amino alcohols, into novel non-proteinogenic alpha-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues. (c) 2004 Elsevier Ltd. All rights reserved.

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页码：3403 / 3417

页数：15

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