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

页码：8590 / 8594

页数：5

共 74 条

[71] Asymmetric conjugate addition reactions of Meldrum's acid derived acceptors employing chiral phosphoramidite ligands [J].

Watanabe, T ;

Knöpfel, TF ;

Carreira, EM .

ORGANIC LETTERS, 2003, 5 (24) :4557-4558

[72] Conjugate addition of diethylzinc to α,β-unsaturated lactones catalyzed by copper-phosphite complexes [J].

Yan, M ;

Zhou, ZY ;

Chan, ASC .

CHEMICAL COMMUNICATIONS, 2000, (02) :115-116

[73] Enantioselective conjugate addition of diethylzinc to enones catalyzed by a copper complex of chiral aryl diphosphite [J].

Yan, M ;

Yang, LW ;

Wong, KY ;

Chan, ASC .

CHEMICAL COMMUNICATIONS, 1999, (01) :11-12

[74] Recent progress in asymmetric allylic substitutions catalyzed by chiral copper complexes [J].

Yorimitsu, H ;

Oshima, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4435-4439

← 1 2 3 4 5 6 7 8 →