The effect of the substrate structure on the stereoselectivity in an asymmetric hydrogenation of unsaturated carboxylic acids over cinchonidine-modified palladium catalyst

被引:36
|
作者
Sugimura, T [1 ]
Watanabe, J [1 ]
Okuyama, T [1 ]
Nitta, Y [1 ]
机构
[1] Univ Hyogo, Himeji Inst Technol, Grad Sch Mat Sci, Kamigori, Hyogo 6781297, Japan
关键词
D O I
10.1016/j.tetasy.2005.03.020
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An enantiomeric ratio of 10: 1 (82% ee) was achieved for the first time in the hydrogenation of alpha,beta-tinsaturated acids with heterogeneous catalysts by designing the substrate structure to enhance the interaction with the catalyst, and to increase the intrinsic stereoselectivity. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1573 / 1575
页数:3
相关论文
共 46 条
  • [21] SOLVENT EFFECT ON ENANTIOSELECTIVE HYDROGENATION OF (E)-ALPHA-PHENYLCINNAMIC ACID WITH CINCHONIDINE-MODIFIED PALLADIUM CATALYSTS
    NITTA, Y
    KOBIRO, K
    CHEMISTRY LETTERS, 1995, (02) : 165 - 165
  • [22] Enantio selective hydrogenation of fluorinated unsaturated carboxylic acids over cinchona alkaloid modified palladium catalysts
    Szollosi, Gyorgy
    Varga, Tibor
    Felfoldi, Karoly
    Cserenyi, Szabolcs
    Bartok, Mihaly
    CATALYSIS COMMUNICATIONS, 2008, 9 (03) : 421 - 424
  • [23] New phenomenon in competitive hydrogenation of binary mixtures of activated ketones over unmodified and cinchonidine-modified Pt/alumina catalyst
    Balazsik, Katalin
    Szori, Kornel
    Szollosi, Gyoergy
    Bartok, Mihaly
    CATALYSIS COMMUNICATIONS, 2011, 12 (15) : 1410 - 1414
  • [24] Solvent effect on the structure sensitivity in enantioselective hydrogenation of α, β-unsaturated acids with modified palladium catalysts
    Nitta, Y
    Kubota, T
    Okamoto, Y
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 212 (1-2) : 155 - 159
  • [25] Asymmetric Catalysis on Cinchonidine-Modified Pt/Al2O3: Kinetics and Isotope Effect in the Hydrogenation of Trifluoroacetophenone
    Meemken, Fabian
    Baiker, Alfons
    Dupre, Jonathan
    Hungerbuehler, Konrad
    ACS CATALYSIS, 2014, 4 (01): : 344 - 354
  • [26] A combined experimental and theoretical study of 1-phenylpropane-1,2-dione hydrogenation over heterogeneous cinchonidine-modified Pt catalyst
    Toukoniitty, E
    Nieminen, V
    Taskinen, A
    Päivärinta, J
    Hotokka, M
    Murzin, DY
    JOURNAL OF CATALYSIS, 2004, 224 (02) : 326 - 339
  • [27] Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination
    Szollosi, Gyoergy
    Herman, Beata
    Szabados, Erika
    Fueloep, Ferenc
    Bartok, Mihaly
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2010, 333 (1-2) : 28 - 36
  • [28] Importance of product desorption in enantioselective hydrogenation of (E)-α-phenylcinnamic acid with a cinchonidine-modified Pd/TiO2 catalyst:: Effect of additives
    Nitta, Y
    CHEMISTRY LETTERS, 1999, (07) : 635 - 636
  • [29] Electrocatalytic asymmetric hydrogenation of α,β-unsaturated acids in a PEM reactor with cinchona-modified palladium catalysts
    Fukazawa, Atsushi
    Tanaka, Kenta
    Hashimoto, Yasushi
    Sato, Yasushi
    Atobe, Mahito
    ELECTROCHEMISTRY COMMUNICATIONS, 2020, 115
  • [30] Kinetic Study of Asymmetric Hydrogenation of α, β-Unsaturated Carboxylic Acid Over Cinchona-Modified Pd/Al2O3 Catalyst
    Shuai Tan
    John R. Monnier
    Christopher T. Williams
    Topics in Catalysis, 2012, 55 : 512 - 517