Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds

被引：57
|
作者：
Kanai, M
Nakagawa, Y
Tomioka, K [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
[2] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
来源：
TETRAHEDRON | 1999年 / 55卷 / 13期
基金：
日本学术振兴会; 日本科学技术振兴机构;
关键词：
asymmetric reactions; catalysis; Grignard reagents;
D O I：
10.1016/S0040-4020(99)00095-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A catalytic asymmetric conjugate addition reaction of organocopper reagents, generated from copper salt, a chiral phosphine, and Grignard reagent, with cyclohexenone is highly dependent on the counter anion of copper species, solvents, Grignard reagents, and the structure of the chiral phosphine. The reaction using the combination of 8 mol% of copper iodide, 32 mol% of the amidophosphine 3, and 1.2 equiv of organomagnesium chloride with cyclohexenone in ether at -78 degrees C gave the 3-substituted cyclohexanone in up to 92% ee and 90% yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3843 / 3854
页数：12
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