The use of new carboranylphosphite ligands in the asymmetric Rh-catalyzed hydrogenation

被引:29
|
作者
Lyubimov, Sergey E. [1 ]
Kuchurov, Ilya V. [2 ]
Tyutyunov, Andrey A. [1 ]
Petrovskii, Pavel V. [1 ]
Kalinin, Valery N. [1 ]
Zlotin, Sergei G. [2 ]
Davankov, Vadim A. [1 ]
Hey-Hawkins, Evamarie [3 ]
机构
[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
[2] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[3] Inst Anorgan Chem, D-04103 Leipzig, Germany
基金
俄罗斯基础研究基金会;
关键词
Asymmetric hydrogenation; Rhodium; Supercritical carbon dioxide; Carboranylphosphite ligands; SUPERCRITICAL CARBON-DIOXIDE; ALPHA-DEHYDROAMINO ACIDS; ENANTIOSELECTIVE HYDROGENATION; PHOSPHORAMIDITE LIGANDS; OLEFIN-HYDROGENATION; CHIRAL PHOSPHITES; EFFICIENT LIGANDS; COMPLEXES; H-8-MONOPHOS; CARBORANES;
D O I
10.1016/j.catcom.2009.11.012
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of new monodentate phosphite ligands based on carboranes have been synthesized and used for asymmetric Rh-catalyzed hydrogenation of prochiral olefins in CH(2)Cl(2) with the result of up to 99.5% ee. High reactivities (100% conversion in 45-60 min) and enantioselectivities (up to 92%) were obtained in the hydrogenation of dimethyl itaconate in supercritical CO(2), In this case the catalytic performance is affected greatly by hydrogen and total pressures. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:419 / 421
页数:3
相关论文
共 50 条
  • [41] P-Chirogenic phosphonium salts: preparation and use in Rh-catalyzed asymmetric hydrogenation of enamides
    Danjo, H
    Sasaki, W
    Miyazaki, T
    Imamoto, T
    TETRAHEDRON LETTERS, 2003, 44 (17) : 3467 - 3469
  • [42] Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: A new class of practical Ligands for Rh-catalyzed asymmetric hydrogenation
    Hu, XP
    Zheng, Z
    ORGANIC LETTERS, 2004, 6 (20) : 3585 - 3588
  • [43] Modular P-chirogenic aminophosphane-phosphinite ligands for Rh-catalyzed asymmetric hydrogenation:: A new model for prediction of enantioselectivity
    Darcel, Christophe
    Moulin, Dominique
    Henry, Jean-Christophe
    Lagrelette, Michael
    Richard, Philippe
    Harvey, Pierre D.
    Juge, Sylvain
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (13) : 2078 - 2090
  • [44] P-Chirogenic Diphosphazanes with Axially Chiral Substituents and Their Use in Rh-Catalyzed Asymmetric Hydrogenation
    Moritz, Jan-Ole
    Chakrabortty, Soumyadeep
    Mueller, Bernd H.
    Spannenberg, Anke
    Kamer, Paul C. J.
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (22): : 14537 - 14544
  • [45] Supramolecular chiral dendritic monophosphites assembled by hydrogen bonding and their use in the Rh-catalyzed asymmetric hydrogenation
    Li, Yong
    He, Yan-Mei
    Li, Zhi-Wei
    Zhang, Feng
    Fan, Qing-Hua
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (09) : 1890 - 1895
  • [46] Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Lactate Precursors in Propylene Carbonate
    Schaeffner, Benjamin
    Andrushko, Vasyl
    Holz, Jens
    Verevkin, Sergey P.
    Boerner, Armin
    CHEMSUSCHEM, 2008, 1 (11) : 934 - 940
  • [47] Synthesis of a tertiary carbinamide via a novel Rh-catalyzed asymmetric hydrogenation
    Limanto, John
    Shultz, C. Scott
    Dorner, Benjamin
    Desmond, Richard A.
    Devine, Paul N.
    Krska, Shane W.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (04): : 1639 - 1642
  • [48] First chiral phosphite with a quaternary ammonium fragment: Synthesis and use in Rh-catalyzed asymmetric hydrogenation
    S. E. Lyubimov
    V. A. Davankov
    P. M. Valetskii
    P. V. Petrovskii
    M. G. Maksimova
    K. N. Gavrilov
    Russian Chemical Bulletin, 2006, 55 : 1448 - 1451
  • [49] First chiral phosphite with a quaternary ammonium fragment: synthesis and use in Rh-catalyzed asymmetric hydrogenation
    Lyubimov, S. E.
    Davankova, V. A.
    Valelskii, P. M.
    Petrovskii, P. V.
    Maksimova, M. G.
    Gavrilov, K. N.
    RUSSIAN CHEMICAL BULLETIN, 2006, 55 (08) : 1448 - 1451
  • [50] Highly Enantioselective Synthesis of Chiral γ-Lactams by Rh-Catalyzed Asymmetric Hydrogenation
    Lang, Qiwei
    Gu, Guoxian
    Cheng, Yaoti
    Yin, Qin
    Zhang, Xumu
    ACS CATALYSIS, 2018, 8 (06): : 4824 - 4828