The tetrahydrooxazinone way to enantiopure α-amino acids:: Synthesis of cis and trans 3-vinyl pipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties

被引：20

作者：

Agami, C ^{[1
]}

Bihan, D ^{[1
]}

Hamon, L ^{[1
]}

Puchot-Kadouri, C ^{[1
]}

机构：

[1] Univ Pierre & Marie Curie, Lab Synth Asymetr, CNRS, UMR 7611, F-75005 Paris, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00486-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of glyoxal with a derivative of (R)-phenylglycinol having an allylsilane side-chain afforded a transient iminium ion. Intramolecular reaction of the iminium ion and the allylsilane moieties occurred in a totally stereoselective way. Straightforward transformations ultimately led to enantiopure either cis or trans 3-vinyl pipecolic acid methyl ester. The stereochemical course of this reaction was rationalized via AMI calculations. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10309 / 10316

页数：8

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