Enantioselective conjugate addition of dialkylzinc to cyclic enones catalyzed by chiral binaphthyldiamine-copper(I) complexes

被引：11
|
作者：
Hatano, Manabu [1 ]
Asai, Takafumi [1 ]
Ishihara, Kazuaki [1 ]
机构：
[1] Nagoya Univ, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4646603, Japan
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 49期
关键词：
D O I：
10.1016/j.tetlet.2007.10.061
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective conjugate addition of dialkylzinc (R2Zn) to cyclic enones was examined using chiral binaphthyldiamine-copper(I) catalysts. Under the present reaction conditions, chiral C-2-symmetric [RZn(II)](2)-diamine-Cu(I) complexes were formed from chiral binaphthyldiamine, R2Zn, and copper(I or II) chloride in situ. The reaction of 2-cyclohexenone with Et2Zn proceeded smoothly in the presence of the corresponding chiral copper(I) complex (5 mol %) and achiral 2,6-diphenylaniline (10 mol %), and the desired Et-adduct was obtained with up to 76% ee in 95% yield. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8590 / 8594
页数：5
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