Design of a new bifunctional asymmetric catalyst from carbohydrates: application to catalytic asymmetric cyanosilylation of aldehydes and acetophenone

被引：74

作者：

Kanai, M ^{[1
]}

Hamashima, Y ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 14期

关键词：

bifunctional asymmetric catalyst; Lewis acid; Lewis base; cyanosilylation; conformation;

D O I：

10.1016/S0040-4039(00)00174-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new active Lewis acid-Lewis base bifunctional asymmetric catalyst 7 was developed using carbohydrate as a scaffold and this catalyst was applied to the asymmetric cyanosilylation of aldehydes and acetophenone. The beta(-)Ph group at the 6-position of 7 was found to be important for a high asymmetric induction (up to 80% ee) by bringing the Al and the phosphine oxide at optimum positions for a dual activation of carbonyl compounds and TMSCN. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2405 / 2409

页数：5

共 16 条

[11] A PEPTIDE ALUMINUM COMPLEX AS A NOVEL CHIRAL LEWIS ACID - ASYMMETRIC ADDITION OF CYANOTRIMETHYLSILANE TO ALDEHYDES [J].