Iridium-catalyzed asymmetric hydrogenation of unfunctionalized tetrasubstituted Olefins

被引:110
|
作者
Schrems, Marcus G. [1 ]
Neumann, Eva [1 ]
Pfaltz, Andreas [1 ]
机构
[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland
关键词
asymmetric catalysis; hydrogenation; iridium; N; P ligands; tetrasubstituted olefins;
D O I
10.1002/anie.200702555
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Even notoriously unreactive substrates such as tetrasubstituted unfunctionalized olefins can be hydrogenated with high efficiency and excellent enantioselectivity using readily accessible chiral Ir catalysts. In this way, two adjacent stereogenic centers can be introduced in a single step (see scheme for an example; BArF = tetrakis(3,5- di(trifluoromethyl)-phenyl)borate, o-Tol = ortho-tolyl). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8274 / 8276
页数:3
相关论文
共 50 条
  • [1] Enantioselectivity in the Iridium-Catalyzed Hydrogenation of Unfunctionalized Olefins
    Church, Tamara L.
    Rasmussen, Torben
    Andersson, Pher G.
    ORGANOMETALLICS, 2010, 29 (24) : 6769 - 6781
  • [2] 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
  • [3] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Enamines
    Baeza, Alejandro
    Pfaltz, Andreas
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (10) : 2266 - 2269
  • [4] PHOSPHINOMETHYL-OXAZOLINES AS EFFICIENT LIGANDS FOR THE IRIDIUM-CATALYZED ENANTIOSELECTIVE HYDROGENATION OF UNFUNCTIONALIZED TETRASUBSTITUTED OLEFINS
    Schrems, Marcus G.
    Neumann, Eva
    Pfaltz, Andreas
    HETEROCYCLES, 2008, 76 (01) : 771 - 781
  • [5] Iridium-catalyzed asymmetric hydrogenation of olefins
    Roseblade, Stephen J.
    Pfaltz, Andreas
    ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (12) : 1402 - 1411
  • [6] Iridium-Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Exocyclic Olefins: An Efficient Access to Dexmethylphenidate
    Tian, Yingying
    Zhu, Yu-Yi
    Yu, Jianchao
    Liu, Dong-Huang
    Yin, Qin
    Ni, Shao-Fei
    Bai, Shao-Tao
    Zhang, Xumu
    CCS CHEMISTRY, 2023, 5 (12): : 2808 - 2817
  • [7] Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins
    Bigler, Raphael
    Mack, Kyle A.
    Shen, Jeff
    Tosatti, Paolo
    Han, Chong
    Bachmann, Stephan
    Zhang, Haiming
    Scalone, Michelangelo
    Pfaltz, Andreas
    Denmark, Scott E.
    Hildbrand, Stefan
    Gosselin, Francis
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (07) : 2844 - 2849
  • [8] Recent progress in iridium-catalyzed enantioselective hydrogenation: Tetrasubstituted olefins and polyenes
    Schrems, Marcus G.
    Wang, Aie
    Pfaltz, Andreas
    CHIMIA, 2008, 62 (06) : 506 - 509
  • [9] Iridium-Catalyzed Enantioselective Hydrogenation of α,β-Unsaturated Carboxylic Acids with Tetrasubstituted Olefins
    Song, Song
    Zhu, Shou-Fei
    Li, Yu
    Zhou, Qi-Lin
    ORGANIC LETTERS, 2013, 15 (14) : 3722 - 3725
  • [10] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Exocyclic C=C Bonds
    Xia, Jingzhao
    Yang, Guoqiang
    Zhuge, Ruijing
    Liu, Yangang
    Zhang, Wanbin
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (51) : 18354 - 18357