Heterogeneous asymmetric addition of diethylzinc to aromatic aldehydes catalyzed by Ti(IV)/imine bridged poly(R)-binaphthol

被引:46
作者
Dong, C
Zhang, JL
Zheng, WH
Zhang, LF
Yu, ZL [1 ]
Choi, MCK
Chan, ASC
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu, Peoples R China
[2] Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China
[3] Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
关键词
D O I
10.1016/S0957-4166(00)00190-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Heterogeneous asymmetric addition of diethylzinc to aldehydes catalyzed by chiral polymer catalysts has been achieved. The conjugated polymers based on a BINOL skeleton were synthesized in five steps and applied to this reaction with yield and e.e. up to 95 and 84.5%, respectively. These chiral polymers can be easily quantitatively recovered and reused without decreasing the e.e. or catalytic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2449 / 2454
页数:6
相关论文
共 22 条
[1]   Synthesis and evaluation of a chiral heterogeneous transfer hydrogenation catalyst [J].
Bayston, DJ ;
Travers, CB ;
Polywka, MEC .
TETRAHEDRON-ASYMMETRY, 1998, 9 (12) :2015-2018
[2]  
Cheng H, 1996, TETRAHEDRON-ASYMMETR, V7, P3083
[3]  
Dong CE, 2000, CHINESE CHEM LETT, V11, P29
[4]   Highly effective soluble polymer-supported catalysts for asymmetric hydrogenation [J].
Fan, QH ;
Ren, CY ;
Yeung, CH ;
Hu, WH ;
Chan, ASC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (32) :7407-7408
[5]  
HU QS, 1995, TETRAHEDRON-ASYMMETR, V6, P2123
[6]   The first optically active and sterically regular poly(1,1'-bi-2-naphthol)s: Precursors to a new generation of polymeric catalysts [J].
Hu, QS ;
Zheng, XF ;
Pu, L .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5200-5201
[7]   New and improved ligands for highly enantioselective catalytic diphenylzinc additions to aryl aldehydes [J].
Huang, WS ;
Pu, L .
TETRAHEDRON LETTERS, 2000, 41 (02) :145-149
[8]   The first highly enantioselective catalytic diphenylzinc additions to aldehydes: Synthesis of chiral diarylcarbinols by asymmetric catalysis [J].
Huang, WS ;
Pu, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4222-4223
[9]   From highly enantioselective monomeric catalysts to highly enantioselective polymeric catalysts: Application of rigid and sterically regular chiral binaphthyl polymers to the asymmetric synthesis of chiral secondary alcohols [J].
Huang, WS ;
Hu, QS ;
Pu, L .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7940-7956
[10]   Development of highly enantioselective polymeric catalysts using rigid and sterically regular chiral polybinaphthols [J].
Huang, WS ;
Hu, QS ;
Zheng, XF ;
Anderson, J ;
Pu, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4313-4314