Iridium-Catalyzed Asymmetric Hydrogenation of α-Alkylidene Succinimides

被引:102
作者
Liu, Yuanyuan [1 ]
Zhang, Wanbin [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; hydrogenation; iridium; ligand effects; synthetic methods; HIGHLY ENANTIOSELECTIVE HYDROGENATION; SPIRO AMINOPHOSPHINE LIGANDS; DIELS-ALDER REACTIONS; OXAZOLINE LIGANDS; 1,3-DIPOLAR CYCLOADDITIONS; ALLYLIC ALKYLATION; CARBONYL-COMPOUNDS; C(SP(3))-H BONDS; CHIRAL SWITCH; COMPLEXES;
D O I
10.1002/anie.201209126
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Not to be out PhOXed! The title reaction provides a new approach to chiral succinimide derivatives with excellent yields and ee values by using a low catalyst loading (0.05 mol %) and mild reaction conditions. Chiral 3-benzyl pyrrolidines and 1-hydroxypyrrolidine-2,5-diones, important structural motifs in natural products and pharmaceuticals, could be readily prepared. BARF -=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2203 / 2206
页数:4
相关论文
共 50 条
  • [11] Iridium-catalyzed asymmetric hydrogenation of unfunctionalized tetrasubstituted Olefins
    Schrems, Marcus G.
    Neumann, Eva
    Pfaltz, Andreas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (43) : 8274 - 8276
  • [12] Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Carboxylic Acids
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (04) : 988 - 1001
  • [13] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized, Trialkyl-Substituted Olefins
    Wang, Aie
    Fraga, Rui P. A.
    Hoermann, Esther
    Pfaltz, Andreas
    CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) : 599 - 606
  • [14] Iridium-Catalyzed Enantioselective Hydrogenation of Indole and Benzofuran Derivatives
    Ge, Yao
    Wang, Zheng
    Han, Zhaobin
    Ding, Kuiling
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (67) : 15482 - 15486
  • [15] Development of iridium-catalyzed asymmetric hydrogenation: New catalysts, new substrate scope
    Cadu, Alban
    Andersson, Pher G.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 714 : 3 - 11
  • [16] Iridium-Catalyzed Asymmetric Hydrogenation of N-Protected Indoles
    Baeza, Alejandro
    Pfaltz, Andreas
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (07) : 2036 - 2039
  • [17] Chiral N-Heterocyclic Carbene/Pyridine Ligands for the Iridium-Catalyzed Asymmetric Hydrogenation of Olefins
    Schumacher, Andreas
    Bernasconi, Maurizio
    Pfaltz, Andreas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7422 - 7425
  • [18] Recent Advances in Iridium-Catalyzed Asymmetric Hydrogenation: New Catalysts, Substrates and Applications in Total Synthesis
    Ganic, Adnan
    Rageot, Denise
    Troendlin, Lars
    Pfaltz, Andreas
    CHIMIA, 2012, 66 (04) : 187 - 191
  • [19] Highly Efficient and Enantioselective Iridium-Catalyzed Asymmetric Hydrogenation of N-Arylimines
    Li, Wei
    Hou, Guohua
    Chang, Mingxin
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (18) : 3123 - 3127
  • [20] Iridium-Catalyzed Enantioselective Hydrogenation of Cyclic Imines
    Chang, Mingxin
    Li, Wei
    Hou, Guohua
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3121 - 3125