General and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives

被引：108

作者：

Kato, N

Suzuki, M

Kanai, M

Shibasaki, M ^{[1
]}

机构：

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

[2] Univ Tokyo, PRESTO, Japan Sci & Technol Corp, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 15期

基金：

日本学术振兴会;

关键词：

asymmetric catalysis; Strecker reaction; ketoimines; disubstituted amino acids; additive effect;

D O I：

10.1016/j.tetlet.2004.02.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Significant improvement in enantioselectivity and catalyst activity was achieved for the catalytic enantio selective Strecker reaction. Using a catalyst (1-2.5 mol%) prepared from Gd((OPr)-Pr-i)(3) and D-glucose derived ligand 1, and in the presence of 2,6-dimethylphenol as an additive, high enantioselectivity was obtained from a wide range of ketoimines, including heteroaromatic and cyclic ketoimines. The new method was applied to an efficient catalytic asymmetric synthesis of sorbinil, a therapeutic agent for diabetic complications. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3147 / 3151

页数：5

共 14 条

[11] Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quaternary amino acids [J].