STEREOSELECTIVE ADDITION-REACTIONS OF CHIRAL N-BENZYLIDENE-PARA-TOLUENESULFINAMIDES - ASYMMETRIC SYNTHESES OF BETA-AMINO AND GAMMA-AMINO ACIDS

被引：141

作者：

HUA, DH

MIAO, SW

CHEN, JS

IGUCHI, S

机构：

[1] Department of Chemistry, Kansas State University, Manhattan

[2] Ono Pharmaceutical Co

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 01期

关键词：

D O I：

10.1021/jo00001a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitrile with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate. Treatment of 2 with allylmagnesium bromide in ether at 0-degrees-C gave the adducts (R)-7 with excellent stereoselectivity. Pure chiral sulfinamides 7 were converted into chiral beta- and gamma-amino acids in four and five steps, respectively.

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页码：4 / 6

页数：3

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