Diastereoselective synthesis of highly substituted 2,5-diaminohexanes via nitrile oxide cycloaddition to a vinylogous amino acid

被引：0
|
作者：
Schreiner, EP
Gstach, H
机构：
来源：
SYNLETT | 1996年 / 11期
关键词：
vinylogous amino acid; nitrile oxide; isoxazoline; reduction; borane-dimethylsulfide complex;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel route to 1,6-disubstituted 2,5-diamino-3-hydroxy-4-hydroxymethylhexanes is described. N-protected ethyl (2E,4S)-4-amino-5-phenylpent-2-enoate undergoes cycloaddition with nitrile oxides producing the syn and anti isomers of ethyl isoxazoline-4-carboxylates in a 2 : 1 ratio. The individual isomers are converted into 1,4-diaminohexanes via chemoselective ester reduction with lithium aluminum hydride, followed by highly diastereoselective reductive cleavage of the isoxazoline ring with borane-dimethylsulfide complex.
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页码：1131 / &
页数：4
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