Stereoselective synthesis of (1R,2R)-1-amino-2-hydroxycyclobutanecarboxylic acid -: serine derivative -: from racemic or optically active 2-benzyloxycyclobutanone

被引：12
|
作者：
Hazelard, Damien [1 ]
Fadel, Antoine [1 ]
Girard, Christian [1 ]
机构：
[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, Lab Synthese Organ & Methodol, UMR 8182, F-91405 Orsay, France
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 09期
关键词：
D O I：
10.1016/j.tetasy.2006.05.014
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An easy and efficient one-pot reaction from readily available 2-benzyloxycyclobutanone gave, by means of an asymmetric Strecker synthesis, a kinetic or thermodynamic nitrile with good selectivity. After separation, the major trans-amino nitrile underwent basic hydrolysis and hydrogenolysis, followed by acidic hydrolysis, to give optically active (1R,2R)-1-amino-2-hydroxycyclobutanecarboxylic acid, serine derivative. The absolute configuration has been established by X-ray analysis of the corresponding cis-amino nitrile. (c) 2006 Elsevier Ltd. All rights reserved.
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收藏
页码：1457 / 1464
页数：8
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