Aqueous enantioselective hydrogenations involving silica-heterogenised catalysts

被引:24
作者
Jamis, J [1 ]
Anderson, JR [1 ]
Dickson, RS [1 ]
Campi, EM [1 ]
Jackson, WR [1 ]
机构
[1] Monash Univ, Dept Chem, Clayton, Vic 3800, Australia
基金
澳大利亚研究理事会;
关键词
rhodium; ruthenium; asymmetric hydrogenation; aqueous solution; heterogenised catalyst; silica;
D O I
10.1016/S0022-328X(00)00127-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A mesoporous silica (HMS) has been prepared with an average pore size of 26 Angstrom. The pores have been shown to include typical chiral catalysts for enantioselective hydrogenation viz Rh-BPPM and Ru-BINAP. The heterogenised catalysts have been shown to be effective for hydrogenations of water-soluble alkenes, e.g. itaconic acid 3 and the sodium salt of N-acetamidocinnamic acid (1a). Modest enantioselectivity was achieved for hydrogenation of the cinnamic acid derivative (40-60% ee) but only poor values for the itaconic acid (0 less than or equal to 16% ee). In some cases, the catalysts could be recovered and reused without significant loss of activity or selectivity. (C) 2000 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:80 / 85
页数:6
相关论文
共 34 条
  • [1] ASYMMETRIC HYDROGENATION WITH NEW CHIRAL FUNCTIONALIZED BISPHOSPHINE-RHODIUM COMPLEXES
    ACHIWA, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (25) : 8265 - 8266
  • [2] CHIRAL SULFONATED PHOSPHINES - SYNTHESES AND USE AS LIGANDS IN ASYMMETRIC HYDROGENATION USING AN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEM
    AMRANI, Y
    LECOMTE, L
    SINOU, D
    BAKOS, J
    TOTH, I
    HEIL, B
    [J]. ORGANOMETALLICS, 1989, 8 (02) : 542 - 547
  • [3] HYDROFORMYLATION BY SUPPORTED AQUEOUS-PHASE CATALYSIS - A NEW CLASS OF HETEROGENEOUS CATALYSTS
    ARHANCET, JP
    DAVIS, ME
    MEROLA, JS
    HANSON, BE
    [J]. NATURE, 1989, 339 (6224) : 454 - 455
  • [4] A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES
    BECK, JS
    VARTULI, JC
    ROTH, WJ
    LEONOWICZ, ME
    KRESGE, CT
    SCHMITT, KD
    CHU, CTW
    OLSON, DH
    SHEPPARD, EW
    MCCULLEN, SB
    HIGGINS, JB
    SCHLENKER, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) : 10834 - 10843
  • [5] Berner E, 1939, LIEBIGS ANN CHEM, V538, P1
  • [6] Preparation of new chiral dioxomolybdenum complexes heterogenised on modified USY-zeolites - Efficient catalysts for selective epoxidation of allylic alcohols
    Corma, A
    Fuerte, A
    Iglesias, M
    Sanchez, F
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 107 (1-3) : 225 - 234
  • [7] NEW RHODIUM COMPLEXES ANCHORED ON MODIFIED USY ZEOLITES - A REMARKABLE EFFECT OF THE SUPPORT ON THE ENANTIOSELECTIVITY OF CATALYTIC-HYDROGENATION OF PROCHIRAL ALKENES
    CORMA, A
    IGLESIAS, M
    DELPINO, C
    SANCHEZ, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) : 1253 - 1255
  • [8] Heterogenised catalysts on zeolites. Synthesis of new chiral Rh(I) complexes with (2S,4R)-trans-4-RCOO-2-(t-butylaminocarbonyl)pyrrolidines and (2S,4S)-cis-4-RCONH-2-(t-butylaminocarbonyl)pyrrolidines. Heterogenisation on silica and a USY-zeolite and study of the role of support on their catalytic profile in hydrogenation of olefins
    Corma, A
    Iglesias, M
    Mohino, F
    Sanchez, F
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 544 (02) : 147 - 156
  • [9] Palladium complexes of phosphine functionalised carbosilane dendrimers as catalysts in a continuous flow membrane reactor
    de Groot, D
    Eggeling, EB
    de Wilde, JC
    Kooijman, H
    van Haaren, RJ
    van der Made, AW
    Spek, AL
    Vogt, D
    Reek, JNH
    Kamer, PCJ
    van Leeuwen, PWNM
    [J]. CHEMICAL COMMUNICATIONS, 1999, (17) : 1623 - 1624
  • [10] Enantioselection using modified zeolite catalysts
    Feast, S
    Bethell, D
    Page, PCB
    King, F
    Rochester, CH
    Siddiqui, MRH
    Willock, DJ
    Hutchings, GJ
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 107 (1-3) : 291 - 295