Asymmetric Synthesis of All Stereoisomers of α-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key Step

被引：36

作者：

Dietz, Friedrich R. ^{[1
]}

Groeger, Harald ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, D-91054 Erlangen, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 24期

关键词：

acylation; amino acids; asymmetric catalysis; rearrangements; stereoselective synthesis; AMINO-ACIDS; BETA-HYDROXY; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; REDUCTION; THREONINE; COMPLEXES; DIASTEREOMERS; VANCOMYCIN; MIGRATION;

D O I：

10.1055/s-0029-1217140

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthetic route to all four stereoisomers of alpha-methylthreonine has been established. Each type of stereoisomer has been isolated in diastereomerically pure form and with an enantiomeric excess of at least 86% ee. The key step in this multi-step synthesis is an enantioselective organocatalytic Steglich rearrangement reaction of O-acetylated azlactones. The Steglich rearrangement was also extended to other substrates.

引用

页码：4208 / 4218

页数：11

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