First synthesis of (1S,2S)- and (1R,2R)-1-amino-2-isopropylcyclobutanecarboxylic acids by asymmetric Strecker reaction from 2-substituted cyclobutanones

被引：37
|
作者：
Truong, M [1 ]
Lecornué, F [1 ]
Fadel, A [1 ]
机构：
[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, CNRS, Lab Carbocycles, F-91405 Orsay, France
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 08期
关键词：
D O I：
10.1016/S0957-4166(03)00073-9
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An efficient and easy one-pot reaction from readily available racemic 2-substituted cyclobutanones gave, by means of asymmetric Strecker synthesis in the presence of an amine chiral auxiliary, two major aminonitriles with excellent diastereoselectivity. After separation, the major cis-aminonitriles were hydrolysed and hydrogenolysed to lead for the first time to pure non-racemic (+)-1-amino-2-isopropylcyclobutanecarboxylic acid (ACBC) and its antipode. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1063 / 1072
页数：10
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