NEW CHIRAL BIS(OXAZOLINYL)BIPYRIDINE LIGAND (BIPYMOX) - ENANTIOSELECTION IN THE ASYMMETRIC HYDROSILYLATION OF KETONES

被引:112
作者
NISHIYAMA, H
YAMAGUCHI, S
PARK, SB
ITOH, K
机构
[1] School of Materials Science, Toyohashi University of Technology, Toyohashi, 441, Tempaku-cho
关键词
D O I
10.1016/S0957-4166(00)86024-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A homochiral chiral 6,6'-bis(oxazolinyl)-2,2'-bipyridine ligand, bipymox (1), and its rhodium complex were synthesized to examine the enantioselectivity in the asymmetric hydrosilylation of ketones in comparison to other chiral oxazoline ligands such as bis-(oxazolinyl)pyridine, pybox (2), and mono(oxazolinyl)pyridine, pymox (3). The bipymox-rhodium catalyst gave the (S)-absolute configuration of the product 1-phenylethanol (90 %ee) in the reduction of acetophenone with diphenylsilane the same as the pybox-rhodium system but opposite to the pymox-rhodium system. The reduction of 4-tert-butylcyclohexanone was also described.
引用
收藏
页码:143 / 150
页数:8
相关论文
共 23 条
[1]   MODELING THE PICHLER-SCHULZ MECHANISM BY CATALYTIC HYDROSILYLATION OF ACYL METAL-COMPLEXES [J].
AKITA, M ;
MITANI, O ;
MOROOKA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (09) :527-529
[2]   CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].
BOLM, C ;
SCHLINGLOFF, G ;
HARMS, K .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1191-1203
[3]   ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE PYRIDINE-DERIVATIVES AND C-2-SYMMETRICAL 2,2'-BIPYRIDINES [J].
BOLM, C ;
EWALD, M ;
FELDER, M ;
SCHLINGLOFF, G .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1169-1190
[4]   CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINC COMPOUNDS TO CHALCONES [J].
BOLM, C ;
EWALD, M ;
FELDER, M .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1205-1215
[5]   ASYMMETRIC CATALYSIS .45. ENANTIOSELECTIVE HYDROSILYLATION OF KETONES WITH [RH(COD)CL]2/PYRIDINYLOXAZOLINE CATALYSTS [J].
BRUNNER, H ;
OBERMANN, U .
CHEMISCHE BERICHTE-RECUEIL, 1989, 122 (03) :499-507
[6]   ENANTIOSELECTIVE CATALYSIS .74. LIGAND EXCESS AND INTERMEDIATES IN THE RHODIUM-CATALYZED ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE WITH PYRIDINEOXAZOLINE LIGANDS [J].
BRUNNER, H ;
BRANDL, P .
TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :919-930
[7]   ASYMMETRIC CATALYSIS .56. ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE WITH A RHODIUM PICOLINEOXAZOLINE CATALYST 1-1 [J].
BRUNNER, H ;
BRANDL, P .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 390 (03) :C81-C83
[8]   LIGAND STRUCTURE AND COMPLEXATION .13. 2,2'-BIPYRIDINE AS A BUILDING BLOCK FOR NEW AZA CROWN ETHERS AND CRYPTANDS [J].
BUHLEIER, E ;
WEHNER, W ;
VOGTLE, F .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (01) :200-204
[9]   SYNTHESIS OF C2-SYMMETRY 2,2'-BIPYRIDINE AND 1,10-PHENANTHROLINE CHIRAL LIGANDS BEARING THE 6,6-DIMETHYLNORPINAN-2-YL GROUP [J].
CHELUCCI, G ;
FALORNI, M ;
GIACOMELLI, G .
TETRAHEDRON, 1992, 48 (17) :3653-3658
[10]   OPTICALLY-ACTIVE PHENANTHROLINES IN ASYMMETRIC CATALYSIS .4. ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE BY RHODIUM CHIRAL ALKYL PHENANTHROLINE CATALYSTS [J].
GLADIALI, S ;
PINNA, L ;
DELOGU, G ;
GRAF, E ;
BRUNNER, H .
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :937-942