DIASTEREOSELECTIVE PREPARATION OF CYCLOPROPANE AMINO-ACIDS - SYNTHESIS OF NORCORONAMIC ACID

被引：0
|
作者：
GAUCHER, A
OLLIVIER, J
SALAUN, J
机构：
来源：
SYNLETT | 1991年 / 03期
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D O I：
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中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 2-(benzylamino)-4-chlorobutyronitrile (3b), resulting from the addition of benzylamine to the cyanohydrin 2 (4-chloro-2-hydroxybutyronitrile), undergoes Swern N-oxidation followed by quantitative base-induced cyclization to provide the 1-aminocyclopropanecarboxylic acid (ACC) precursor 5d (1-benzylideneaminocyclopropanecarbonitrile). Analogously prepared from the chiral beta-hydroxyester 7 [(S)-(+)-methyl 3-hydroxy-2-methylpropionate], the nitrile amines 10a,b [2-(benzylamino)-4-chloro-3-methylbutyronitrile] undergo Swern N-oxidation and diastereoselective cyclization leading readily to the natural Norcoronamic acid [6; (1S,2S)-1-amino-2-methylcyclopropanecarboxylic acid (ds > 84%)].
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页码：151 / 153
页数：3
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