TRIARYLCARBENIUM IONS AS CATALYSTS IN THE MUKAIYAMA ALDOL ADDITION - A MECHANISTIC INVESTIGATION

被引：76

作者：

DENMARK, SE

CHEN, CT

机构：

[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 25期

关键词：

ALDOL CONDENSATION; TRIARYLCARBENIUM IONS; DIASTEREOSELECTIVE;

D O I：

10.1016/S0040-4039(00)73345-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Phenyl-2:3,6:7-dibenzosuberyl salts 5(+) efficiently catalyze the aldol reaction between silyl enol ethers and benzaldehyde with moderate diastereoselectivity. Crossover experiments with doubly labeled silyl enol ethers, kinetic and stereochemical studies identify 5(+) as the catalyst rather than a Lewis acidic R(3)SiX species in this transformation.

引用

页码：4327 / 4330

页数：4

共 27 条

[1] STERICALLY HINDERED SILYL PERCHLORATES AS BLOCKING REAGENTS [J].