Optically active β-ketoiminato cationic cobalt(III) complexes:: Efficient catalysts for enantioselective carbonyl-ene reaction of glyoxal derivatives

被引：60

作者：

Kezuka, S ^{[1
]}

Ikeno, T ^{[1
]}

Yamada, T ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 12期

关键词：

D O I：

10.1021/ol015980m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHCIS] Optically active beta -ketoiminato cationic cobalt(lll) complexes were synthesized as effective Lewis acid catalysts for the enantioselective carbonylene reaction, In the presence of a catalytic amount of cobalt(lll) hexafluoroantimonate derived from the optically active 1,2-diphenyl-1,2-ethanediamine, the carbonyl-ene reaction with a variety of alkenes and glyoxal derivatives smoothly proceeded to afford the corresponding homoallylic alcohols in good-to high yields with high enantioselectivities.

引用

页码：1937 / 1939

页数：3

共 39 条

[1] Enantioselective carbonyl-ene reaction of glyoxal derivatives catalyzed by cationic 3-oxobutylideneaminatocobalt(III) complexes
Kezuka, S
Kogami, Y
Ikeno, T
Yamada, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2003, 76 (01) : 49 - 58
[2] Enantioselective carbonyl-ene reaction of glyoxal derivatives catalyzed by cationic 3-oxobutylideneaminatocobalt(III) complexes
Kezuka, S., 1600, Chemical Society of Japan (76):
[3] Optically active cationic cobalt(III) complexes: Highly efficient catalysts for enantioselective hetero Diels-Alder reaction
Kezuka, S
Mita, T
Ohtsuki, N
Ikeno, T
Yamada, T
CHEMISTRY LETTERS, 2000, (07) : 824 - 825
[4] Enantioselective Cationic Polyene Cyclization vs Enantioselective Intramolecular Carbonyl-Ene Reaction
Zhao, Yu-Jun
Li, Bin
Tan, Li-Jun Serena
Shen, Zhi-Liang
Loh, Teck-Peng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) : 10242 - 10244
[5] 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
[6] 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
[7] Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Bronsted acids as efficient catalysts
Rueping, Magnus
Theissmann, Thomas
Kuenkel, Alexander
Koenigs, Rene M.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) : 6798 - 6801
[8] Enantioselective Carbonyl-Ene Reactions Catalyzed by Chiral Cationic Dirhodium(II,III) Carboxamidates
Xu, Xichen
Wang, Xiaochen
Liu, Yuxiao
Doyle, Michael P.
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24): : 12185 - 12190
[9] OPTICALLY-ACTIVE BETA-KETOIMINATO MANGANESE(III) COMPLEXES AS EFFICIENT CATALYSTS IN ENANTIOSELECTIVE AEROBIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS
NAGATA, T
IMAGAWA, K
YAMADA, T
MUKAIYAMA, T
INORGANICA CHIMICA ACTA, 1994, 220 (1-2) : 283 - 287
[10] Lewis acid platinum complexes of conformationally flexible NUPHOS diphosphines: Highly efficient catalysts for the carbonyl-ene reaction
Doherty, S
Goodrich, P
Hardacre, C
Luo, HK
Nieuwenhuyzen, M
Rath, RK
ORGANOMETALLICS, 2005, 24 (24) : 5945 - 5955

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