ASYMMETRIC HYDROGENATION OF PROCHIRAL CARBOXYLIC-ACIDS AND FUNCTIONALIZED CARBONYL-COMPOUNDS CATALYZED BY RUTHENIUM(II)-BINAP COMPLEXES WITH ARYL NITRILES (BINAP = (R)-S,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL OR (S)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL)

被引:31
作者
SHAO, LM [1 ]
TAKEUCHI, K [1 ]
IKEMOTO, M [1 ]
KAWAI, T [1 ]
OGASAWARA, M [1 ]
TAKEUCHI, H [1 ]
KAWANO, H [1 ]
SABURI, M [1 ]
机构
[1] UNIV TOKYO,FAC ENGN,DEPT IND CHEM,BUNKYO KU,TOKYO 113,JAPAN
关键词
D O I
10.1016/0022-328X(92)83466-U
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Complexes RuCl2(ArCN)2(binap), II (binap = (R)- or (S)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; ArCN = benzonitrile, a; 2-furancarbonitrile, b; pentafluorobenzonitrile, c) were prepared, and their solution properties were investigated by P-31 NMR measurements. The catalytic activities and enantioselectivities for IIa-c catalysed hydrogenation of some prochiral acids were very similar to those provided by Ru2Cl4(binap)2(NEt3), I. In the hydrogenation of beta-functionalized carbonyl compounds, however, IIa-c showed considerably lower activities and/or selectivities, compared with complex I. The differences in IIa-c catalysed reactions are discussed in relation to the coordinating abilities of ArCN in II.
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页码:133 / 147
页数:15
相关论文
共 17 条
[1]   CHEMISTRY AND SYNTHESIS OF LIGNAN(-)-CUBEBIN [J].
BATTERBEE, JE ;
BURDEN, RS ;
CROMBIE, L ;
WHITING, DA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2470-+
[2]   NEW COMPLEXES OF RUTHENIUM(2) WITH TRIPHENYLPHOSPHINE AND OTHER LIGANDS [J].
GILBERT, JD ;
WILKINSO.G .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1969, (12) :1749-&
[3]   SYNTHESIS OF NOVEL CHIRAL RUTHENIUM COMPLEXES OF 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL AND THEIR USE AS ASYMMETRIC CATALYSTS [J].
IKARIYA, T ;
ISHII, Y ;
KAWANO, H ;
ARAI, T ;
SABURI, M ;
YOSHIKAWA, S ;
AKUTAGAWA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (13) :922-924
[4]   RUTHENIUM(II)-BINAP CATALYZED STEREOSELECTIVE HOMOGENEOUS HYDROGENATION OF 1,3-DIKETONES [J].
KAWANO, H ;
ISHII, Y ;
SABURI, M ;
UCHIDA, Y .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (02) :87-88
[5]   ASYMMETRIC HYDROGENATION OF PROCHIRAL ALKENES CATALYZED BY RUTHENIUM COMPLEXES OF (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL [J].
KAWANO, H ;
IKARIYA, T ;
ISHII, Y ;
SABURI, M ;
YOSHIKAWA, S ;
UCHIDA, Y ;
KUMOBAYASHI, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (09) :1571-1575
[6]  
KAWANO H, IN PRESS B CHEM SOC
[7]   SYNTHESIS OF NEW CATIONIC BINAP-RUTHENIUM(II) COMPLEXES AND THEIR USE IN ASYMMETRIC HYDROGENATION [BINAP = 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL] [J].
MASHIMA, K ;
KUSANO, KH ;
OHTA, T ;
NOYORI, R ;
TAKAYA, H .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) :1208-1210
[8]   SYNTHESIS OF 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP), AN ATROPISOMERIC CHIRAL BIS(TRIARYL)PHOSPHINE, AND ITS USE IN THE RHODIUM(I)-CATALYZED ASYMMETRIC HYDROGENATION OF ALPHA-(ACYLAMINO)ACRYLIC ACIDS [J].
MIYASHITA, A ;
YASUDA, A ;
TAKAYA, H ;
TORIUMI, K ;
ITO, T ;
SOUCHI, T ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7932-7934
[9]   2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) - A NEW ATROPISOMERIC BIS(TRIARYL)PHOSPHINE - SYNTHESIS AND ITS USE IN THE RH(I)-CATALYZED ASYMMETRIC HYDROGENATION OF ALPHA-(ACYLAMINO)ACRYLIC ACIDS [J].
MIYASHITA, A ;
TAKAYA, H ;
SOUCHI, T ;
NOYORI, R .
TETRAHEDRON, 1984, 40 (08) :1245-1253
[10]   RUTHENIUM-CATALYZED OXIDATIVE TRANSFORMATION OF ALCOHOLS AND ALDEHYDES TO ESTERS AND LACTONES [J].
MURAHASHI, SI ;
NAOTA, T ;
ITO, K ;
MAEDA, Y ;
TAKI, H .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4319-4327