Enantioselective hydrogenation of 2'-chloroacetophenone with ((R)-Binap)Ru(O2CAr)(2) complexes: Influence of carboxylate ligands and solvents

被引:17
作者
Doucet, H [1 ]
LeGendre, P [1 ]
Bruneau, C [1 ]
Dixneuf, PH [1 ]
Souvie, JC [1 ]
机构
[1] ORIL SA,F-76210 BOLBEC,FRANCE
关键词
D O I
10.1016/0957-4166(96)00036-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New (Binap)Ru(carboxylate)(2) have been prepared and used for the enantioselective hydrogenation of 2'-chloroacetophenone. Both enantiomers of 2'-chlorophenylethanol can be selectively prepared with the same optically active catalyst precursor simply by changing the solvent, and the carboxylate groups have an influence on the enantioselectivity only in aprotic solvents.
引用
收藏
页码:525 / 528
页数:4
相关论文
共 16 条
[1]   ASYMMETRIC-SYNTHESIS BY METAL BINAP CATALYSTS [J].
AKUTAGAWA, S .
APPLIED CATALYSIS A-GENERAL, 1995, 128 (02) :171-207
[2]   KINETICS AND MECHANISM OF CATALYSIS OF THE ASYMMETRIC HYDROGENATION OF ALPHA-BETA-UNSATURATED CARBOXYLIC-ACIDS BY BIS(CARBOXYLATO)(2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)-RUTHENIUM(II), [RUII(BINAP)(O2CR)2] [J].
ASHBY, MT ;
HALPERN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :589-594
[3]  
BEERENS FC, 1995, TETRAHEDRON-ASYMMETR, V6, P1105
[4]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[5]   GENERAL-SYNTHESIS OF NOVEL CHIRAL RUTHENIUM CATALYSTS AND THEIR USE IN ASYMMETRIC HYDROGENATION [J].
GENET, JP ;
MALLART, S ;
PINEL, C ;
JUGE, S ;
LAFFITTE, JA .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :43-46
[6]   ENANTIOSELECTIVE HYDROGENATION REACTIONS WITH A FULL SET OF PREFORMED AND PREPARED IN-SITU CHIRAL DIPHOSPHINE-RUTHENIUM(II) CATALYSTS [J].
GENET, JP ;
PINEL, C ;
RATOVELOMANANAVIDAL, V ;
MALLART, S ;
PFISTER, X ;
BISCHOFF, L ;
DEANDRADE, MCC ;
DARSES, S ;
GALOPIN, C ;
LAFFITTE, JA .
TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :675-690
[7]   NEW EFFICIENT METHODS FOR THE SYNTHESIS AND INSITU PREPARATION OF RUTHENIUM(II) COMPLEXES OF ATROPISOMERIC DIPHOSPHINES AND THEIR APPLICATION IN ASYMMETRIC CATALYTIC HYDROGENATIONS [J].
HEISER, B ;
BROGER, EA ;
CRAMERI, Y .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :51-62
[8]   HOMOGENEOUS ASYMMETRIC HYDROGENATION OF FUNCTIONALIZED KETONES [J].
KITAMURA, M ;
OHKUMA, T ;
INOUE, S ;
SAYO, N ;
KUMOBAYASHI, H ;
AKUTAGAWA, S ;
OHTA, T ;
TAKAYA, H ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :629-631
[9]   A PRACTICAL ASYMMETRIC-SYNTHESIS OF CARNITINE [J].
KITAMURA, M ;
OHKUMA, T ;
TAKAYA, H ;
NOYORI, R .
TETRAHEDRON LETTERS, 1988, 29 (13) :1555-1556
[10]   PRACTICAL SYNTHESIS OF BINAP-RUTHENIUM(II) DICARBOXYLATE COMPLEXES [J].
KITAMURA, M ;
TOKUNAGA, M ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :4053-4054