BINOL derived monodentate acylphosphite ligands for homogeneously catalyzed enantioselective hydrogenation

被引:26
|
作者
Korostylev, A
Monsees, A
Fischer, C
Borner, A
机构
[1] Univ Rostock, Leibniz Inst Organ Katal, D-18055 Rostock, Germany
[2] Degussa AG, Projekthuas Katal, Geschaftsbereich Creavis, Ind Hoechst, D-65926 Frankfurt, Germany
[3] Univ Rostock, Fachbereich Chem, D-18059 Rostock, Germany
关键词
D O I
10.1016/j.tetasy.2004.01.012
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiopure acylphosphites have been prepared based upon chiral nonsubstituted and 3,3'-disubstituted binaphthols in order to elucidate steric and electronic effects on the Rh(I)-catalyzed asymmetric hydrogenation of functionalized olefins. With these new types of ligands, up to 80% ee was obtained. Rate as well as enantio selectivity of the hydrogenation were strongly dependent on the precatalyst preparation and substitution pattern of the ligand. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1001 / 1005
页数:5
相关论文
共 50 条
  • [1] Highly enantioselective rhodium-catalyzed hydrogenation with monodentate ligands
    van den Berg, M
    Minnaard, AJ
    Schudde, EP
    van Esch, J
    de Vries, AHM
    de Vries, JG
    Feringa, BL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11539 - 11540
  • [2] Modular monodentate phosphoramidite ligands for rhodium-catalyzed enantioselective hydrogenation
    Liu, Y
    Ding, KL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) : 10488 - 10489
  • [3] Modular monodentate phosphoramidite ligands for rhodium-catalyzed enantioselective hydrogenation
    Liu, Yan
    Ding, Kuiling
    1600, American Chemical Society, Columbus, United States (127):
  • [4] Enantioselective hydrogenation of β-ketoesters with monodentate ligands
    Junge, K
    Hagemann, B
    Enthaler, S
    Oehme, G
    Michalik, M
    Monsees, A
    Riermeier, T
    Dingerdissen, U
    Beller, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) : 5066 - 5069
  • [5] Highly enantioselective hydrogenation of enamides catalyzed by rhodium-monodentate phosphoramidite complex derived from H8-BINOL
    Li, XS
    Jia, X
    Lu, G
    Au-Yeung, TTL
    Lam, KH
    Lo, TWH
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2003, 14 (18) : 2687 - 2691
  • [6] Asymmetric hydrogenation of quinolines catalyzed by iridium complexes of monodentate BINOL-derived phosphoramidites
    Mrsic, Natasa
    Lefort, Laurent
    Boogers, Jeroen A. F.
    Minnaard, Adriaan J.
    Feringa, Ben L.
    de Vries, Johannes G.
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) : 1081 - 1089
  • [7] Enantioselective Rh-catalyzed hydrogenation of vinyl carboxylates with monodentate phosphite ligands
    Reetz, MT
    Goossen, LJ
    Meiswinkel, A
    Paetzold, J
    Jensen, JF
    ORGANIC LETTERS, 2003, 5 (17) : 3099 - 3101
  • [8] Monodentate chiral spiro phosphoramidites: Efficient ligands for rhodium-catalyzed enantioselective hydrogenation of enamides
    Hu, AG
    Fu, Y
    Xie, JH
    Zhou, H
    Wang, LX
    Zhou, QL
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (13) : 2348 - 2350
  • [9] Advances of rhodium-catalyzed enantioselective hydrogenation of functional olefins - The thriving of monodentate phosphorous ligands
    Zeng, QL
    Mi, AQ
    Jiang, YH
    PROGRESS IN CHEMISTRY, 2004, 16 (04) : 603 - 612
  • [10] Highly enantioselective or not? -: Chiral monodentate monophosphorus ligands in the asymmetric hydrogenation
    Komarov, IV
    Börner, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (07) : 1197 - +