Metal-Catalyzed Asymmetric Hydrogenation of C=N Bonds

被引：89
作者：
Abdine, Racha Abed Ali [1 ]
Hedouin, Gaspard [1 ]
Colobert, Francoise [1 ]
Wencel-Delord, Joanna [1 ]
机构：
[1] Univ Haute Alsace, Univ Strasbourg, Lab Innovat Mol & Applicat, ECPM,UMR CNRS 7042, F-67087 Strasbourg, France
来源：
ACS CATALYSIS | 2021年 / 11卷 / 01期
关键词：
asymmetric hydrogenation; metal-catalysis; imine; chiral amine; ligand; HIGHLY ENANTIOSELECTIVE HYDROGENATION; PHOSPHINE-PHOSPHORAMIDITE LIGANDS; IRIDIUM COMPLEXES; TRANSITION-METAL; IMINE HYDROGENATION; CHIRAL DIPHOSPHINE; OXAZOLINE LIGANDS; CYCLIC IMINES; DIASTEREOSELECTIVE HYDROGENATION; ACYCLIC IMINES;
D O I：
10.1021/acscatal.0c03353
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：
This Review recaps the achievements in the field of metal-catalyzed asymmetric direct hydrogenation of nonactivated and activated imines. A summary of the reported catalytic systems with the corresponding reactivity, selectivity, and limitations is given including a discussion about the effects of some reaction conditions on the enantioselectivity of imine hydrogenation. An analysis of proposed imine hydrogenation mechanisms is discussed.
引用
收藏
页码：215 / 247
页数：33
相关论文
共 141 条
  • [1] RuHCl(diphosphine)(diamine): Catalyst precursors for the stereoselective hydrogenation of ketones and imines
    Abdur-Rashid, K
    Lough, AJ
    Morris, RH
    [J]. ORGANOMETALLICS, 2001, 20 (06) : 1047 - 1049
  • [2] Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives
    Abe, H
    Amii, H
    Uneyama, K
    [J]. ORGANIC LETTERS, 2001, 3 (03) : 313 - 315
  • [3] The first example of asymmetric hydrogenation of imines with Co2(CO)8/(R)-BINAP as catalytic precursor
    Amezquita-Valencia, Manuel
    Cabrera, Armando
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2013, 366 : 17 - 21
  • [4] 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
  • [5] [Anonymous], US, Patent No. [6822118 B1, 6822118]
  • [6] Asymmetric Hydrogenation of N-Arylimines Catalyzed by the Xyl-Skewphos/DPEN-Ruthenium(II) Complex
    Arai, Noriyoshi
    Utsumi, Noriyuki
    Matsumoto, Yuki
    Murata, Kunihiko
    Tsutsumi, Kunihiko
    Ohkuma, Takeshi
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2089 - 2095
  • [7] Iridium-Catalyzed Asymmetric Hydrogenation of Imines
    Baeza, Alejandro
    Pfaltz, Andreas
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) : 4003 - 4009
  • [8] RHODIUM(I) SULFONATED-BDPP CATALYZED ASYMMETRIC HYDROGENATION OF IMINES IN AQUEOUS ORGANIC 2-PHASE SOLVENT SYSTEMS
    BAKOS, J
    OROSZ, A
    HEIL, B
    LAGHMARI, M
    LHOSTE, P
    SINOU, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (23) : 1684 - 1685
  • [9] A FACILE METHOD FOR THE PREPARATION OF 2,4-BIS(DIPHENYLPHOSPHINO)PENTANE (BDPP) ENANTIOMERS AND THEIR APPLICATION IN ASYMMETRIC HYDROGENATION
    BAKOS, J
    TOTH, I
    HEIL, B
    MARKO, L
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 279 (1-2) : 23 - 29
  • [10] CATALYTIC ASYMMETRIC HYDROGENATION OF IMINES - USE OF RHODIUM(I)/PHOSPHINE COMPLEXES AND CHARACTERIZATION OF RHODIUM(I)/IMINE COMPLEXES
    BECALSKI, AG
    CULLEN, WR
    FRYZUK, MD
    JAMES, BR
    KANG, GJ
    RETTIG, SJ
    [J]. INORGANIC CHEMISTRY, 1991, 30 (26) : 5002 - 5008
12345678910