HIGHLY STEREOCONTROLLED SEQUENTIAL ASYMMETRIC MICHAEL ADDITION-REACTIONS WITH CINNAMATE ESTERS - GENERATION OF 3 AND 4 CONTIGUOUS STEREOGENIC CENTERS ON 7-CARBON ACYCLIC MOTIFS

被引：33

作者：

HANESSIAN, S

GOMTSYAN, A

机构：

[1] Department of Chemistry, Montréal, Que. H3C 3J7, Universite Montreal P.O. Box 6128, Succ. Centre-ville

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)78330-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of allyl and crotyl bicyclic chiral phosphonamide anions with two cinnamate esters leads to a sequential Michael reaction with excellent diastereoselectivity. The option to quench enolates with methyl iodide greatly enhances the versatility of the reaction in the synthesis of acyclic seven-carbon chains with vicinal and alternating C-methyl and C-phenyl substituents.

引用

页码：7509 / 7512

页数：4

共 26 条

[1] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].