Chiral C2-symmetric figands containing two binaphthyl units linked by 2,2′-bipyridyl bridge in asymmetric catalysis

被引:8
作者
Bai, XL [1 ]
Kang, CQ [1 ]
Liu, XD [1 ]
Gao, LX [1 ]
机构
[1] Chinese Acad Sci, Grad Sch, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China
关键词
D O I
10.1016/j.tetasy.2004.12.015
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The catalytic activities of new chiral C-2-symmetric ligands 1-4 in the asymmetric alkylation of aromatic aldehydes with diethylzinc to give 1-arylpropanols are studied. In most cases, the yields were good and enantioselectivities up to 87% were observed. Copper-catalyzed cyclopropanation proceeded with less than or equal to51% enantioselectivity and similar to3 :1 trans/cis-diastereoselectivity. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:727 / 731
页数:5
相关论文
共 48 条
[1]   Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)indoline [J].
Asami, M ;
Watanabe, H ;
Honda, K ;
Inoue, S .
TETRAHEDRON-ASYMMETRY, 1998, 9 (23) :4165-4173
[2]   OPTICALLY-ACTIVE BIPYRIDINES IN ASYMMETRIC CATALYSIS [J].
BOLM, C ;
ZEHNDER, M ;
BUR, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02) :205-207
[3]   Chiral ligands with pyridine donors in transition metal catalyzed enantioselective cyclopropanation and hydrosilylation reactions [J].
Chelucci, G ;
Gladiali, S ;
Sanna, MG ;
Brunner, H .
TETRAHEDRON-ASYMMETRY, 2000, 11 (16) :3419-3426
[4]   Modified BINOL ligands in asymmetric catalysis [J].
Chen, Y ;
Yekta, S ;
Yudin, AK .
CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211
[5]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[6]   SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .1. SYNTHESIS OF CHIRAL SEMICORRIN LIGANDS AND GENERAL CONCEPTS [J].
FRITSCHI, H ;
LEUTENEGGER, U ;
SIEGMANN, K ;
PFALTZ, A ;
KELLER, W ;
KRATKY, C .
HELVETICA CHIMICA ACTA, 1988, 71 (06) :1541-1552
[7]   CHIRAL COPPER SEMICORRIN COMPLEXES AS ENANTIOSELECTIVE CATALYSTS FOR THE CYCLOPROPANATION OF OLEFINS BY DIAZO-COMPOUNDS [J].
FRITSCHI, H ;
LEUTENEGGER, U ;
PFALTZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (11) :1005-1006
[8]   SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .2. ENANTIOSELECTIVE CYCLOPROPANE FORMATION FROM OLEFINS WITH DIAZO-COMPOUNDS CATALYZED BY CHIRAL (SEMICORRINATO)COPPER COMPLEXES [J].
FRITSCHI, H ;
LEUTENEGGER, U ;
PFALTZ, A .
HELVETICA CHIMICA ACTA, 1988, 71 (06) :1553-1565
[9]   THE FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CHEMOTACTIC FACTOR SIRENIN BY AN INTRAMOLECULAR [2+1] CYCLIZATION USING A NEW CHIRAL CATALYST [J].
GANT, TG ;
NOE, MC ;
COREY, EJ .
TETRAHEDRON LETTERS, 1995, 36 (48) :8745-8748
[10]   Direct catalytic asymmetric Michael reaction of hydroxyketones:: Asymmetric Zn catalysis with a Et2Zn/linked-BINOL complex [J].
Harada, S ;
Kumagai, N ;
Kinoshita, T ;
Matsunaga, S ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2582-2590