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
  • [1] Iridium-Catalyzed Asymmetric Hydrogenation of Imines
    Baeza, Alejandro
    Pfaltz, Andreas
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) : 4003 - 4009
  • [2] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Enamines
    Baeza, Alejandro
    Pfaltz, Andreas
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (10) : 2266 - 2269
  • [3] Iridium-Catalyzed Asymmetric Hydrogenation
    Margalef, Jessica
    Pamies, Oscar
    Dieguez, Montserrat
    IRIDIUM CATALYSTS FOR ORGANIC REACTIONS, 2021, 69 : 153 - 205
  • [4] Iridium-catalyzed asymmetric hydrogenation of vinyl ethers
    Zhu, Ye
    Burgess, Kevin
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) : 979 - 983
  • [5] Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
    Cadu, Alban
    Upadhyay, Puspesh K.
    Andersson, Pher G.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (12) : 1061 - 1065
  • [6] Iridium-Catalyzed Asymmetric Hydrogenation of Pyridinium Salts
    Ye, Zhi-Shi
    Chen, Mu-Wang
    Chen, Qing-An
    Shi, Lei
    Duan, Ying
    Zhou, Yong-Gui
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (40) : 10181 - 10184
  • [7] SpinPhox/Iridium(I)-Catalyzed Asymmetric Hydrogenation of Cyclic α-Alkylidene Carbonyl Compounds
    Liu, Xu
    Han, Zhaobin
    Wang, Zheng
    Ding, Kuiling
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) : 1978 - 1982
  • [8] Methylaluminoxane as an Alternative for BArF in the Iridium-Catalyzed Asymmetric Hydrogenation of Imines
    Mrsic, Natasa
    Panella, Lavinia
    IJpeij, Edwin G.
    Minnaard, Adriaan J.
    Feringa, Ben L.
    de Vries, Johannes G.
    CHEMCATCHEM, 2011, 3 (07) : 1139 - 1142
  • [9] Iridium-Catalyzed Asymmetric Hydrogenation of Quinoline Derivatives with C3*-TunePhos
    Gou, Fa-Rong
    Li, Wei
    Zhang, Xumu
    Liang, Yong-Min
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (14-15) : 2441 - 2444
  • [10] Mechanistic insights into iridium-catalyzed asymmetric hydrogenation of dienes
    Cui, XH
    Fan, YB
    Hall, MB
    Burgess, K
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (23) : 6859 - 6868