Catalytic enantioselective cyanosilylation of ketones: improvement of enantioselectivity and catalyst turn-over by ligand tuning

被引：141

作者：

Hamashima, Y ^{[1
]}

Kanai, M ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 04期

基金：

日本学术振兴会;

关键词：

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

D O I：

10.1016/S0040-4039(00)02039-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sterical and electronical tuning of the bifunctional catalyst 1 afforded the improved catalyst 2, which promoted the cyanosilylation of ketones with higher enantioselectivity as well as with improved catalyst turn-over with a factor of up to 10. Thus, chiral quaternary alpha -hydroxynitriles were obtained with excellent ee (up to 94% ee) using 1 mol% of 2 in the case of aryl ketones and 2.5 mol% of 2 in the case of aliphatic ketones. (C) 2001 Elsevier Science Ltd. All rights: reserved.

引用

页码：691 / 694

页数：4

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