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
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
收藏
页码:1937 / 1939
页数:3
相关论文
共 24 条
[1]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Catalytic enantioselective carbonyl-ene reactions with glyoxylate and pyruvate esters [J].
Evans, DA ;
Tregay, SW ;
Burgey, CS ;
Paras, NA ;
Vojkovsky, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7936-7943
[2]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Enantioselective catalysis of the glyoxylate-ene reaction [J].
Evans, DA ;
Burgey, CS ;
Paras, NA ;
Vojkovsky, T ;
Tregay, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5824-5825
[3]   THERMODYNAMIC BEHAVIOR OF ALKANES IN SUPERACID MEDIA [J].
FABRE, PL ;
DEVYNCK, J ;
TREMILLON, B .
CHEMICAL REVIEWS, 1982, 82 (06) :591-614
[4]   Chiral palladium(II)-catalyzed asymmetric glyoxylate-ene reaction:: Alternative approach to the enantioselective synthesis of α-hydroxy esters [J].
Hao, J ;
Hatano, M ;
Mikami, K .
ORGANIC LETTERS, 2000, 2 (25) :4059-4062
[5]   Highly enantioselective cyclopropanation of styrenes with diazoacetates catalyzed by optically active β-ketoiminato cobalt(II) complexes [J].
Ikeno, T ;
Sato, M ;
Yamada, T .
CHEMISTRY LETTERS, 1999, (12) :1345-1346
[6]   Optically active cationic cobalt(III) complexes: Highly efficient catalysts for enantioselective hetero Diels-Alder reaction [J].
Kezuka, S ;
Mita, T ;
Ohtsuki, N ;
Ikeno, T ;
Yamada, T .
CHEMISTRY LETTERS, 2000, (07) :824-825
[7]  
KEZUKA S, IN PRESS B CHEM SOC
[8]   ASYMMETRIC ENE REACTION CATALYZED BY CHIRAL ORGANO-ALUMINUM REAGENT [J].
MARUOKA, K ;
HOSHINO, Y ;
SHIRASAKA, T ;
YAMAMOTO, H .
TETRAHEDRON LETTERS, 1988, 29 (32) :3967-3970
[9]   CATALYTIC ASYMMETRIC GLYOXYLATE ENE REACTION - A PRACTICAL ACCESS TO ALPHA-HYDROXY ESTERS IN HIGH ENANTIOMERIC PURITIES [J].
MIKAMI, K ;
TERADA, M ;
NAKAI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :3949-3954
[10]   Asymmetric catalysis of carbonyl-ene reactions and related carbon-carbon bond forming reactions [J].
Mikami, K .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :639-644