Effects of ligands and additive alcohols on enantioselection in highly efficient asymmetric borohydride reduction of ketones catalyzed by optically active aldiminato cobalt(II) complexes

被引：0

作者：

Nagata, T ^{[1
]}

Sugi, KD ^{[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：

SYNLETT | 1996年 / 11期

关键词：

enantioselective reduction; ketones; catalytic; cobalt complex; sodium borohydride;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly enantioselective reduction of ketones with sodium borohydride was achieved in the presence of a catalytic amount of optically active aldiminato cobalt(II) complexes to afford the corresponding secondary alcohols in quantitative yields with high enantiomeric excesses. The effects of ligands of the cobalt(II) complexes and of the additive alcohol pairs used for modification of the borohydride on the present reduction were described. The enantiofacial discrimination in the present asymmetric reduction was discussed based on the conformation of the cobalt complex determined by X-ray analysis.

引用

页码：1076 / &

页数：4

共 27 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
Sugi, KD
Nagata, T
Yamada, T
Mukaiyama, T
CHEMISTRY LETTERS, 1996, (09) : 737 - 738
[2] 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):
[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] 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
[5] 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
[6] 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
[7] 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
[8] 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
[9] Optically active aldiminato cobalt(II) complexes as efficient catalysts for enantioselective cyclopropanation of styrenes with diazoacetates
Yamada, T
Ikeno, T
Sekino, H
Sato, M
CHEMISTRY LETTERS, 1999, (08) : 719 - 720
[10] 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

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