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
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.
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页码:5032 / 5034
页数:3
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