RUTHENIUM (II)-SULFONATED BINAP - A NOVEL WATER-SOLUBLE ASYMMETRIC HYDROGENATION CATALYST

被引:58
作者
WAN, KT [1 ]
DAVIS, ME [1 ]
机构
[1] CALTECH, DIV CHEM & CHEM ENGN, PASADENA, CA 91125 USA
关键词
D O I
10.1016/S0957-4166(00)82224-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ruthenium (II)-sulfonated-BINAP has been synthesized and this novel water-soluble complex is shown to be an excellent asymmetric hydrogenation catalyst for 2-acylamino acid precursors and methylenesuccinic acid in both methanolic as well as in neat water solvent systems. Enantiomeric excesses approaching 90% have been obtained in aqueous and methanolic solvents. Effects of solvent, pressure and the addition of organic base on enantioselectivity are described.
引用
收藏
页码:2461 / 2468
页数:8
相关论文
共 33 条
[1]   MECHANISM OF RHODIUM-PROMOTED TRIPHENYLPHOSPHINE REACTIONS IN HYDROFORMYLATION PROCESSES [J].
ABATJOGLOU, AG ;
BILLIG, E ;
BRYANT, DR .
ORGANOMETALLICS, 1984, 3 (06) :923-926
[2]   ASYMMETRIC HYDROGENATION WITH NEW CHIRAL FUNCTIONALIZED BISPHOSPHINE-RHODIUM COMPLEXES [J].
ACHIWA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (25) :8265-8266
[3]   ASYMMETRIC HYDROGENATION IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS USING RHODIUM COMPLEXES OF SULFONATED PHOSPHINES [J].
ALARIO, F ;
AMRANI, Y ;
COLLEUILLE, Y ;
DANG, TP ;
JENCK, J ;
MOREL, D ;
SINOU, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (03) :202-203
[4]   A SIMPLE GENERAL-ROUTE TO CHELATE DIPHOSPHINE RUTHENIUM(II) COMPLEXES [J].
ALCOCK, NW ;
BROWN, JM ;
ROSE, M ;
WIENAND, A .
TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :47-50
[5]   CHIRAL SULFONATED PHOSPHINES - SYNTHESES AND USE AS LIGANDS IN ASYMMETRIC HYDROGENATION USING AN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEM [J].
AMRANI, Y ;
LECOMTE, L ;
SINOU, D ;
BAKOS, J ;
TOTH, I ;
HEIL, B .
ORGANOMETALLICS, 1989, 8 (02) :542-547
[6]   SYNTHESIS AND APPLICATION IN ENANTIOSELECTIVE HYDROGENATION OF A RHODIUM COMPLEX OF AN ASYMMETRIC WATER-SOLUBLE DIPHOSPHINE PGE-17-DIOP [J].
AMRANI, Y ;
SINOU, D .
JOURNAL OF MOLECULAR CATALYSIS, 1984, 24 (02) :231-233
[7]   HYDROFORMYLATION BY SUPPORTED AQUEOUS-PHASE CATALYSIS - A NEW CLASS OF HETEROGENEOUS CATALYSTS [J].
ARHANCET, JP ;
DAVIS, ME ;
MEROLA, JS ;
HANSON, BE .
NATURE, 1989, 339 (6224) :454-455
[8]   RHODIUM(I) SULFONATED-BDPP CATALYZED ASYMMETRIC HYDROGENATION OF IMINES IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS [J].
BAKOS, J ;
OROSZ, A ;
HEIL, B ;
LAGHMARI, M ;
LHOSTE, P ;
SINOU, D .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) :1684-1685
[9]   SYNTHESIS AND APPLICATION OF RHODIUM COMPLEXES OF ASYMMETRIC WATER-SOLUBLE DIPHOSPHINE DERIVED FROM 2-[(DIPHENYLPHOSPHINO)METHYL]-4-(DIPHENYLPHOSPHINO)-PYRROLIDINE [J].
BENHAMZA, R ;
AMRANI, Y ;
SINOU, D .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 288 (02) :C37-C39
[10]  
CHAN ASC, 1993, ACS SYM SER, V517, P27