Catalytic asymmetric borane reduction of prochiral ketones by the use of diazaborolidine catalysts prepared from chiral β-diamines

被引：34
作者：
Sato, S [1 ]
Watanabe, H [1 ]
Asami, M [1 ]
机构：
[1] Yokohama Natl Univ, Fac Engn, Dept Chem & Biotechnol, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan
来源：
TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 21期
关键词：
D O I：
10.1016/S0957-4166(00)00414-6
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral diazaborolidine catalysts prepared in situ from chiral P-diamines and borane. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(4-trifluoromethyl)anilinomethyl]indoline 2f. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4329 / 4340
页数：12
相关论文
共 27 条
[1]   CATALYTIC ENANTIOSELECTIVE DEPROTONATION OF MESO-EPOXIDES BY THE USE OF CHIRAL LITHIUM AMIDE [J].
ASAMI, M ;
ISHIZAKI, T ;
INOUE, S .
TETRAHEDRON-ASYMMETRY, 1994, 5 (05) :793-796
[2]   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
[3]   Enantioselective addition of diethylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine [J].
Asami, M ;
Inoue, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (07) :1687-1690
[4]   ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC TO CHALCONES USING NICL2-CHIRAL BETA-DIAMINE COMPLEX AS CATALYST [J].
ASAMI, M ;
USUI, K ;
HIGUCHI, S ;
INOUE, S .
CHEMISTRY LETTERS, 1994, (02) :297-298
[5]   Catalytic asymmetric borane reduction of prochiral ketones by the use of chiral β-diamines [J].
Asami, M ;
Sato, S ;
Watanabe, H .
CHEMISTRY LETTERS, 2000, (09) :990-991
[6]   ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH CHIRAL HYDRIDE REAGENTS PREPARED FROM LITHIUM ALUMINUM-HYDRIDE AND (S)-2-(N-SUBSTITUTED AMINOMETHYL)PYRROLIDINES [J].
ASAMI, M ;
OHNO, H ;
KOBAYASHI, S ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (06) :1869-1873
[7]   Kinetic resolution of cis-3-alkylcyclohexene oxide by a chiral lithium amide -: An application to a synthesis of both enantiomers of isomenthone [J].
Asami, M ;
Sato, S ;
Honda, K ;
Inoue, S .
HETEROCYCLES, 2000, 52 (03) :1029-+
[8]   BETA-HYDROXYSULFOXIMINES IN THE CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE [J].
BOLM, C ;
FELDER, M .
TETRAHEDRON LETTERS, 1993, 34 (38) :6041-6044
[9]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[10]  
2-Z
123