ASYMMETRIC CONJUGATE ADDITIONS OF CHIRAL ALLYLPHOSPHONAMIDE AND CROTYLPHOSPHONAMIDE ANIONS TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - HIGHLY STEREOCONTROLLED ACCESS TO VICINALLY SUBSTITUTED CARBON CENTERS AND CHEMICALLY ASYMMETRIZED CHIRONS

被引：70

作者：

HANESSIAN, S

GOMTSYAN, A

PAYNE, A

HERVE, Y

BEAUDOIN, S

机构：

[1] Department of Chemistry, Université de Montréal, Montréal, P.Q., H3C 3J7, P.O. Box 6128, Station A

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 19期

关键词：

D O I：

10.1021/jo00071a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of anions derived from chiral nonracemic allyl and crotyl bicyclic phosphonamides with alpha,beta-unsaturated cyclic ketones, esters, lactones, and lactams take place at the gamma-position of the reagents and lead to diastereomerically pure or highly enriched products of conjugate addition. The option to quench the corresponding enolates with various alkyl halides offers a versatile approach to vicinal substitution including the generation of quaternary carbon centers.

引用

页码：5032 / 5034

页数：3

共 40 条

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