Inversion of enantioselectivity in the hydrogenation of ketopantolactone on platinum modified by ether derivatives of cinchonidine

被引：59
|
作者：
Diezi, S
Szabo, A
Mallat, T
Baiker, A
机构：
[1] ETH Honggerberg, Inst Chem & Bioengn, Swiss Fed Inst Technol, CH-8093 Zurich, Switzerland
[2] Ubichem Res Ltd, H-1025 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 17期
关键词：
D O I：
10.1016/S0957-4166(03)00528-7
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Asymmetric hydrogenation of ketopantolactone was studied on a 5 wt% Pt/Al2O3 catalyst in the presence of cinchonidine and its O-methyl. -ethyl. -phenyl and -trimethylsilyl derivatives. Inversion of enantioselectivity with the latter two bulky substituents proved that in the enantiodifferentiating step cinchonidine adsorbs via the quinoline ring lying approximately parallel to the Pt surface. The striking nonlinear effect observed with cinchonidine-O-phenyl-cinchonidine mixtures is attributed to differences in the adsorption strength and geometry of the modifiers. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2573 / 2577
页数：5
相关论文
共 50 条
  • [41] Structure effect of TsDPEN derivatives on enantioselectivity of asymmetric transfer hydrogenation
    Liu, Juntao
    Wu, Yinuo
    Li, Xingshu
    Chan, Albert S. C.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (12) : 2177 - 2180
  • [42] Inversion of enantioselectivity in the 2,2,2-trifluoroacetophenone hydrogenation over Pt-alumina catalyst modified by cinchona alkaloids
    Szori, Kornel
    Balazsik, Katalin
    Cserenyi, Szabolcs
    Szollosi, Gyoergy
    Bartok, Mihaly
    APPLIED CATALYSIS A-GENERAL, 2009, 362 (1-2) : 178 - 184
  • [43] Origins of enantioselectivity in reductions of ketones on cinchona alkaloid modified platinum
    Vayner, G
    Houk, KN
    Sun, YK
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) : 199 - 203
  • [44] Preparation of cinchonidine-modified palladium catalysts for the enantioselective hydrogenation of (E)-α-phenylcinnamic acid
    Nitta, Y
    Kubota, T
    Okamoto, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (11) : 2635 - 2641
  • [45] Competition at chiral metal surfaces:: Fundamental aspects of the inversion of enantioselectivity in hydrogenations on platinum
    Bonalumi, N
    Vargas, A
    Ferri, D
    Bürgi, T
    Mallat, T
    Baiker, A
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) : 8467 - 8477
  • [46] ASYMMETRIC HYDROGENATION OF METHYL PYRUVATE USING PT-C CATALYST MODIFIED WITH CINCHONIDINE
    ORITO, Y
    IMAI, S
    NIWA, S
    NIPPON KAGAKU KAISHI, 1979, (08) : 1118 - 1120
  • [47] Asymmetric synthesis of alpha-alkylproline derivatives from a chiral borane-amine adduct: Inversion of enantioselectivity in the presence of a crown ether
    Ferey, V
    Vedrenne, P
    Toupet, L
    LeGall, T
    Mioskowski, C
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21): : 7244 - 7245
  • [48] CORRELATION OF SOLVATOCHROMIC EFFECT WITH RATE OF CATALYTIC HYDROGENATION OF NITROBENZENE DERIVATIVES ON RANEY NICKEL MODIFIED WITH PLATINUM
    FINKELSH.AV
    KUZMINA, ZM
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY,USSR, 1966, 40 (01): : 83 - &
  • [49] Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3
    Jenkins, Robert L.
    Dummer, Nicholas
    Li, Xiabao
    Bawaked, Salem M.
    McMorn, Paul
    Wells, Richard P. K.
    Burrows, Andrew
    Kiely, Christopher J.
    Hutchings, Graham J.
    CATALYSIS LETTERS, 2006, 110 (1-2) : 135 - 138
  • [50] Molecular dynamics simulations of cinchonidine-modified platinum in ethanol: comparisons with surface studies
    Calvo, SR
    LeBlanc, RJ
    Williams, CT
    Balbuena, PB
    SURFACE SCIENCE, 2004, 563 (1-3) : 57 - 73
12345