Highly enantioselective conjugate addition of diethylzinc to substituted chalcones catalyzed by Cu(II) complexes of a tridentate P,N,O ligand

被引：23

作者：

Biradar, Deepak Baburao ^{[1
]}

Gau, Han-Mou ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 06期

关键词：

D O I：

10.1016/j.tetasy.2008.02.027

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new series of tridentate P,N,O ligands having hard and soft donor atoms derived from chiral amino alcohols were developed and employed in the Cu(II)-catalyzed conjugate addition of diethylzinc to substituted chalcones. The asymmetric additions to a variety of substituted chalcones afforded products in excellent yields and good to excellent enantioselectivities up to 97% ee. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：733 / 738

页数：6

共 70 条

[1] Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc [J].

Alexakis, A ;

Polet, D ;

Rosset, S ;

March, S .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5660-5667

[2]

Alexakis A, 2000, EUR J ORG CHEM, V2000, P4011, DOI 10.1002/1099-0690(200012)2000:24<4011::AID-EJOC4011>3.0.CO

[3]

2-D

[4] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].

Alexakis, A ;

Benhaim, C ;

Rosse, S ;

Humam, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263

[5] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL [J].

Alexakis, A ;

Vastra, J ;

Burton, J ;

Benhaim, C ;

Mangeney, P .

TETRAHEDRON LETTERS, 1998, 39 (43) :7869-7872

[6]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[7] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].

Arnold, LA ;

Imbos, R ;

Mandoli, A ;

de Vries, AHM ;

Naasz, R ;

Feringa, BL .

TETRAHEDRON, 2000, 56 (18) :2865-2878

[8] Chiral aminophosphine-oxazoline auxiliaries applied to copper-catalysed enantioselective 1,4-additions to enones [J].

Blanc, C ;

Agbossou-Niedercorn, F .

TETRAHEDRON-ASYMMETRY, 2004, 15 (05) :757-761

[9]

Brunner H, 1999, EUR J INORG CHEM, P51

[10]

Brunner H, 1998, EUR J INORG CHEM, P43

← 1 2 3 4 5 6 7 →