Catalytic asymmetric borane reduction of prochiral ketones by the use of chiral β-diamines

被引：21

作者：

Asami, M ^{[1
]}

Sato, S ^{[1
]}

Watanabe, H ^{[1
]}

机构：

[1] Yokohama Natl Univ, Fac Engn, Dept Chem & Biotechnol, Hodogaya Ku, Yokohama, Kanagawa 2408501, Japan

来源：

CHEMISTRY LETTERS | 2000年 / 09期

关键词：

D O I：

10.1246/cl.2000.990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The catalytic asymmetric borane reduction of prochiral ketones was examined in the presence of chiral P-diamines. Chiral secondary alcohols were obtained with modest to high enantiomeric excesses (up to 92% ee) using (S)-2-[(p-trifluoromethyl)anilinomethyl]indoline.

引用

页码：990 / 991

页数：2

共 20 条

[1] CATALYTIC ENANTIOSELECTIVE DEPROTONATION OF MESO-EPOXIDES BY THE USE OF CHIRAL LITHIUM AMIDE
ASAMI, M
ISHIZAKI, T
INOUE, S
[J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (05) : 793 - 796
[2] Enantioselective addition of dialkylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)indoline
Asami, M
Watanabe, H
Honda, K
Inoue, S
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (23) : 4165 - 4173
[3] Enantioselective addition of diethylzinc to aldehydes catalyzed by (S)-2-(N,N-disubstituted aminomethyl)pyrrolidine
Asami, M
Inoue, S
[J]. 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
ASAMI, M
USUI, K
HIGUCHI, S
INOUE, S
[J]. CHEMISTRY LETTERS, 1994, (02) : 297 - 298
[5] ASYMMETRIC TRANSFORMATION OF SYMMETRICAL EPOXIDES TO ALLYLIC ALCOHOLS BY LITHIUM (S)-2-(N,N-DISUBSTITUTED AMINOMETHYL)PYRROLIDIDE
ASAMI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (03) : 721 - 727
[6] ASYMMETRIC REDUCTION OF PROCHIRAL KETONES WITH CHIRAL HYDRIDE REAGENTS PREPARED FROM LITHIUM ALUMINUM-HYDRIDE AND (S)-2-(N-SUBSTITUTED AMINOMETHYL)PYRROLIDINES
ASAMI, M
OHNO, H
KOBAYASHI, S
MUKAIYAMA, T
[J]. 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
Asami, M
Sato, S
Honda, K
Inoue, S
[J]. HETEROCYCLES, 2000, 52 (03) : 1029 - +
[8] BETA-HYDROXYSULFOXIMINES IN THE CATALYZED ENANTIOSELECTIVE REDUCTION OF KETONES WITH BORANE
BOLM, C
FELDER, M
[J]. 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

← 1 2 →