Enantioselective borohydride reduction of ketones catalyzed by optically active cobalt(II) complexes: Achievement of high enantioselection by modified borohydrides with furfuryl alcohol derivatives

被引：38

作者：

Sugi, KD ^{[1
]}

Nagata, T ^{[1
]}

Yamada, T ^{[1
]}

Mukaiyama, T ^{[1
]}

机构：

[1] SCI UNIV TOKYO, FAC SCI, DEPT APPL CHEM, SHINJUKU KU, TOKYO 162, JAPAN

来源：

CHEMISTRY LETTERS | 1996年 / 09期

关键词：

D O I：

10.1246/cl.1996.737

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective borohydride reduction of ketones catalyzed by optically active (beta-oxoaldiminato) cobalt(II) complexes was remarkably improved by using the borohydride which was modified with furfuryl alcohol derivatives and ethanol. In the presence of 1 mol% of the above complex catalysts, asymmetric reduction of aromatic ketones proceeded smoothly to give the corresponding optically active alcohols in quantitative yields within 6-12 h with high enantiomeric excesses (90-97% ee).

引用

页码：737 / 738

页数：2

共 18 条

[1] Enantioselective Borohydride Reduction of Ketones Catalyzed by Optically Active Cobalt(II) Complexes: Achievement of High Enantioselection by Modified Borohydrides with Furfuryl Alcohol Derivatives
Chem Lett, 9 (737):
[2] Enantioselective borohydride reduction catalyzed by optically active cobalt complexes
Yamada, T
Nagata, T
Sugi, KD
Yorozu, K
Ikeno, T
Ohtsuka, Y
Miyazaki, D
Mukaiyama, T
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (18) : 4485 - 4509
[3] Practical and efficient enantioselective borohydride reduction of aromatic ketones catalyzed by optically active cobalt(II) complexes using pre-modified borohydride
Sugi, KD
Nagata, T
Yamada, T
Mukaiyama, T
CHEMISTRY LETTERS, 1996, (12) : 1081 - 1082
[4] Enantioselective borohydride reduction catalyzed by optically active β-ketoiminato cobalt complexes
Yamada, T
Nagata, T
Ohtsuka, Y
Ikeno, T
Mukaiyama, T
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (09) : 843 - 856
[5] Effects of ligands and additive alcohols on enantioselection in highly efficient asymmetric borohydride reduction of ketones catalyzed by optically active aldiminato cobalt(II) complexes
Nagata, T
Sugi, KD
Yamada, T
Mukaiyama, T
SYNLETT, 1996, (11) : 1076 - &
[6] ENANTIOSELECTIVE REDUCTION OF KETONES WITH SODIUM-BOROHYDRIDE, CATALYZED BY OPTICALLY-ACTIVE (BETA-OXOALDIMINATO)COBALT(II) COMPLEXES
NAGATA, T
YOROZU, K
YAMADA, T
MUKAIYAMA, T
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (19): : 2145 - 2147
[7] Homogeneous Enantioselective Catalysis in a Continuous-Flow Microreactor: Highly Enantioselective Borohydride Reduction of Ketones Catalyzed by Optically Active Cobalt Complexes
Hayashi, Takuo
Kikuchi, Satoshi
Asano, Yukako
Endo, Yoshishige
Yamada, Tohru
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (06) : 1235 - 1240
[8] Optically active β-ketoiminato cobalt(II) complexes as highly efficient catalysts in enantioselective borohydride reduction of ketones, imines, and α,β-unsaturated carboxylates
Yamada, T
Nagata, T
Ikeno, T
Ohtsuka, Y
Sagara, A
Mukaiyama, T
INORGANICA CHIMICA ACTA, 1999, 296 (01) : 86 - 93
[9] Highly enantioselective borohydride reductions of 2-phenacylpyridine catalyzed by optically active β-ketoiminato cobalt(II) complexes
Ohtsuka, Y
Ikeno, T
Yamada, T
TETRAHEDRON-ASYMMETRY, 2000, 11 (18) : 3671 - 3674
[10] Dynamic kinetic resolution with enantioselective borohydride reduction catalyzed by optically active β-ketoiminato cobalt(II) complexes:: Highly diastereo- and enantioselective preparation of optically active anti-aldol compounds
Ohtsuka, Y
Miyazaki, D
Ikeno, T
Yamada, T
CHEMISTRY LETTERS, 2002, (01) : 24 - 25

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