STEREOCONTROLLED PREPARATION OF CHIRAL SECONDARY ALPHA-METHYLENE GAMMA-LACTAMS BY ADDITION OF ORGANOZINC REAGENTS DERIVED FROM 2-(BROMOMETHYL)ACRYLATES TO IMINES USING BETA-AMINOALCOHOLS AS CHIRAL AUXILIARIES

被引：45

作者：

DEMBELE, YA ^{[1
]}

BELAUD, C ^{[1
]}

VILLIERAS, J ^{[1
]}

机构：

[1] FAC SCI & TECH NANTES,SYNTH ORGAN LAB,CNRS,URA 475,2 RUE DE LA HOUSSINIERE,F-44072 NANTES 03,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(00)80253-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Stereocontrolled addition of isolated organozinc reagents 1, prepared from 2-(bromomethyl)acrylates to imines, can be achieved with d.e. approximately 100% using beta-amino alcohols as chiral auxiliaries. High yields of pure R or S secondary alpha-methylene gamma-lactams can be prepared after a three step elimination of the chiral auxiliary (chloration, dehydrochloration of the resulting beta-chloroamine, acid hydrolysis of enamide).

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页码：511 / 514

页数：4

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