ENANTIOSELECTIVE TRIMETHYLSILYLCYANATION OF SOME ALDEHYDES CATALYZED BY CHIRAL SCHIFF-BASE TITANIUM ALKOXIDE COMPLEXES

被引：213

作者：

HAYASHI, M ^{[1
]}

MIYAMOTO, Y ^{[1
]}

INOUE, T ^{[1
]}

OGUNI, N ^{[1
]}

机构：

[1] YAMAGUCHI UNIV,FAC SCI,DEPT CHEM,YAMAGUCHI 753,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 06期

关键词：

D O I：

10.1021/jo00058a037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of aldehydes (aromatic, heteroaromatic, alpha,beta-unsaturated, and nonconjugate aliphatic aldehydes) has been trimethylsilylcyanated in highly enantiomeric excess (ee) with a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases. A remarkable rate enhancement was brought about by the addition of the Schiff base into the titanium alkoxide mediated silylcyanation of aldehydes. The chemical structure of chiral Schiff base-titanium alkoxide complexes is discussed based on their C-13 NMR spectra, field desorption (FD) mass spectra, and molecular weights.

引用

页码：1515 / 1522

页数：8

共 39 条

[1] CATALYTIC ASYMMETRIC-SYNTHESIS OF CYCLOPROPANE-CARBOXYLIC ACIDS - AN APPLICATION OF CHIRAL COPPER CARBENOID REACTION [J].