The ortho effect:: copper-catalyzed highly enantioselective 1,4-conjugate addition of diethylzinc to chalcones

被引：28

作者：

Liu, LT ^{[1
]}

Wang, MC ^{[1
]}

Zhao, WX ^{[1
]}

Zhou, YL ^{[1
]}

Wang, XD ^{[1
]}

机构：

[1] Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Henan, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 01期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetasy.2005.11.031

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The copper-catalyzed enantioselective 1,4-conjugate addition of diethylzinc to chalcones was investigated in the presence of a catalytic amount of NP-ferrocenyl ligands with central and planar chirality under mild conditions (0 degrees C -> rt). It was found that chalcones with ortho-substituents (from ortho-substituted benzaldehydes and acetophenone/substituted acetophenones) led to a dramatic improvement in the enantio selectivities. The (R)- and (S)-antipodes of the addition reaction were obtained with up to 92% ee after this transformation. (c) 2006 Published by Elsevier Ltd.

引用

页码：136 / 141

页数：6

共 47 条

[41]

PERLMUTER P, 1992, TETRAHEDRON ORGANIC, V9

[42] ASYMMETRIC CONJUGATE ADDITION [J].

ROSSITER, BE ;

SWINGLE, NM .

CHEMICAL REVIEWS, 1992, 92 (05) :771-806

[43] Enantioselective conjugate addition of dialkylzinc and diphenylzinc to enones catalyzed by a chiral copper(I) binaphthylthiophosphoramide or binaphthylselenophosphoramide ligand system [J].

Shi, M ;

Wang, CJ ;

Zhang, W .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (21) :5507-5516

[44]

Sibi MP, 2000, TETRAHEDRON, V56, P8033

[45] Novel chiral copper complexes of NP-ferrocenyl ligands with central and planar chirality as efficient catalyst for asymmetric addition of diethylzinc to immes [J].

Wang, MC ;

Liu, LT ;

Hua, YZ ;

Zhang, JS ;

Shi, YY ;

Wang, DK .

TETRAHEDRON-ASYMMETRY, 2005, 16 (15) :2531-2534

[46]

Xian H., 1988, J ORG CHEM, V53, P4862

[47]

YAMAMOTO Y, 1995, METHODS ORGANIC CHEM, V21, P2041

← 1 2 3 4 5 →