IMMOBILIZATION OF RHODIUM COMPLEXES IN AQUEOUS HBF4 - THE ENANTIOSELECTIVE HYDROGENATION OF PROCHIRAL OLEFINS WITH ([CH3CHP(PARA-C6H4NME2H)2CH2CHP(PARA-C6H4NME2H)2CH3]RHNBD)5+

被引:34
作者
TOTH, I
HANSON, BE
DAVIS, ME
机构
[1] VIRGINIA POLYTECH INST & STATE UNIV,DEPT CHEM,BLACKSBURG,VA 24061
[2] VIRGINIA POLYTECH INST & STATE UNIV,DEPT CHEM ENGN,BLACKSBURG,VA 24061
基金
美国国家科学基金会;
关键词
D O I
10.1016/0022-328X(90)85477-G
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The complex {[CH3CHP(p-C6H4NMe2H)2CH2CHP(p-C6H4NMe2H)2CH3]RhNBD}5+ is active for the enantioselective hydrogenation of cinnamic acid derivatives at low pH in aqueous solutions of the noncoordinating acid HBF4. Analytical data are consistent with protonation occurring exclusively at the dimethylamino groups and not at the metal. Enantiomeric excesses of 67 to 97% are obtained for the hydrogenation of Z-(4-OMe, 3-OAcC6H3CHC(NHC(O)Me)COOH in aqueous HBF4 at 14 bar H2. The use of aqueous acidic solutions allows for the convenient workup of the product and recycling of the catalyst. © 1990.
引用
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页码:363 / 373
页数:11
相关论文
共 35 条
[1]   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
[2]   PHASE-TRANSFER CATALYZED ORGANOMETALLIC CHEMISTRY - COBALT CARBONYL-CATALYZED CARBONYLATION OF HALIDES [J].
ALPER, H ;
ABBAYES, HD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 134 (01) :C11-C14
[3]   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
[4]  
ARHANCET JP, 1989, NATURE, V334, P454
[5]  
ARHANCET JP, IN PRESS J CATAL
[6]   A FACILE METHOD FOR THE PREPARATION OF 2,4-BIS(DIPHENYLPHOSPHINO)PENTANE (BDPP) ENANTIOMERS AND THEIR APPLICATION IN ASYMMETRIC HYDROGENATION [J].
BAKOS, J ;
TOTH, I ;
HEIL, B ;
MARKO, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) :23-29
[7]  
CARTER HE, 1981, J BIOL CHEM, V159, P255
[8]   PHASE-TRANSFER CATALYSIS IN COBALT-CATALYZED CARBONYLATION OF BENZYL HALIDES [J].
CASSAR, L ;
FOA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1977, 134 (01) :C15-C16
[9]   ASYMMETRICAL REDUCTION CATALYZED BY TRANSITION-METAL COMPLEXES .3. CHIRAL DIPHOSPHINES DERIVED FROM ISOPROPYLIDENE-2,3-DIHYDROXY-1,4-BIS(DIPHENYLPHOSPHINO)BUTANE [J].
DANG, TP ;
POULIN, JC ;
KAGAN, HB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 91 (01) :105-115
[10]  
DANG TP, 1987, Patent No. 4654176