AZINOTHRICIN SYNTHETIC STUDIES .1. EFFICIENT ASYMMETRIC SYNTHESES OF (3R)-PIPERAZIC AND (3S)-PIPERAZIC ACIDS

被引：43
|
作者：
HALE, KJ
DELISSER, VM
MANAVIAZAR, S
机构：
[1] The Christopher Ingold Laboratories, Department of Chemistry, University College London, London, WC1H OAJ England
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 49期
关键词：
D O I：
10.1016/S0040-4039(00)60838-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient asymmetric synthesis of both (3R)- and (3S)-piperazic acids has been developed that is based on electrophilic hydrazination of a chiral bromovaleryl carboximide enolate with di-tert-butyl azodicarboxylate, followed by subsequent intramolecular S(N)2 displacement of the bromide by the resulting substituted aza anion. The diastereoselectivity of the process is typically greater than 96%.
引用
收藏
页码：7613 / 7616
页数：4
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