Enantioselective borane reduction of aromatic ketones using chiral BINOL derivatives as ligands in an aluminum catalyst

被引:26
作者
Lin, YM [1 ]
Fu, IP [1 ]
Uang, BJ [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
关键词
D O I
10.1016/S0957-4166(02)00008-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral aluminum complex-catalyzed asymmetric borane reduction of aromatic ketones has been successfully carried out in the presence of (R)-BINOL derivatives as ligands. Secondary alcohols were obtained in high yields with good enantioselectivities (up to 90% e.e.). (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3217 / 3221
页数:5
相关论文
共 33 条
[1]   Regioselective catalytic asymmetric reaction of Horner-Wadsworth-Emmons reagents with enones: The odyssey of chiral aluminum catalysts [J].
Arai, T ;
Sasai, H ;
Yamaguchi, K ;
Shibasaki, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :441-442
[2]   A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].
Arai, T ;
Sasai, H ;
Aoe, K ;
Okamura, K ;
Date, T ;
Shibasaki, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106
[3]   BETA-HYDROXYSULFOXIMINES IN THE CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE [J].
BOLM, C ;
FELDER, M .
TETRAHEDRON LETTERS, 1993, 34 (38) :6041-6044
[4]   Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes [J].
Chan, ASC ;
Zhang, FY ;
Yip, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) :4080-4081
[5]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[6]  
COREY EJ, 1998, ANGEW CHEM INT EDIT, V37, P2012
[7]   HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS [J].
CRAM, DJ ;
HELGESON, RC ;
PEACOCK, SC ;
KAPLAN, LJ ;
DOMEIER, LA ;
MOREAU, P ;
KOGA, K ;
MAYER, JM ;
CHAO, Y ;
SIEGEL, MG ;
HOFFMAN, DH ;
SOGAH, GDY .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1930-1946
[8]   ASYMMETRIC BORON-CATALYZED REACTIONS [J].
DELOUX, L ;
SREBNIK, M .
CHEMICAL REVIEWS, 1993, 93 (02) :763-784
[9]   Chiral hydroxythiols as catalysts for enantioselective borane ketone reductions [J].
Fiaud, JC ;
Mazé, F ;
Kagan, HB .
TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3647-3655
[10]   DIAZABOROLIDINES, A NEW CLASS OF ENANTIOSELECTIVE ORGANOBORON CATALYTIC AGENTS [J].
FROELICH, O ;
BONIN, M ;
QUIRION, JC ;
HUSSON, HP .
TETRAHEDRON-ASYMMETRY, 1993, 4 (11) :2335-2338