Iridium-Catalyzed Enantioselective Hydrogenation of Indole and Benzofuran Derivatives

被引:25
|
作者
Ge, Yao [1 ,2 ]
Wang, Zheng [1 ]
Han, Zhaobin [1 ]
Ding, Kuiling [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
关键词
asymmetric catalysis; benzofurans; benzothiophene; 1; 1-dioxides; hydrogenation; indoles; iridium; CONVERTING ENZYME-INHIBITORS; DNA-POLYMERASE-BETA; ASYMMETRIC HYDROGENATION; MECHANISTIC INSIGHTS; OXAZOLINE LIGANDS; POTENT; ACID; COMPLEXES; PYRIDINE; (+)-MYRISTININ-A;
D O I
10.1002/chem.202002532
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective hydrogenation of a broad spectrum of N-, O-, and S-containing aromatic benzoheterocycles or nonaromatic unsaturated heterocycles has been realized by using an Ir/SpinPHOX (SpinPHOX=spiro[4,4]-1,6-nonadiene-based phosphine-oxazoline) complex as the catalyst, affording an array of the corresponding chiral benzoheterocycles (30 examples) with excellent enantioselectivities (>99 % eein most cases) and turnover numbers up to 500.
引用
收藏
页码:15482 / 15486
页数:5
相关论文
共 50 条
  • [1] Iridium-catalyzed enantioselective hydrogenation of olefins
    Pfaltz, A
    Blankenstein, J
    Hilgraf, R
    Hörmann, E
    McIntyre, S
    Menges, F
    Schönleber, M
    Smidt, SP
    Wüstenberg, B
    Zimmermann, N
    ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) : 33 - 43
  • [2] Iridium-Catalyzed Enantioselective Hydrogenation of Vinylsilanes
    Wang, Aie
    Bernasconi, Maurizio
    Pfaltz, Andreas
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (15) : 2523 - 2529
  • [3] Iridium-catalyzed enantioselective hydrogenation of terminal alkenes
    McIntyre, S
    Hörmann, E
    Menges, F
    Smidt, SP
    Pfaltz, A
    ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) : 282 - 288
  • [4] Iridium-Catalyzed Enantioselective Hydrogenation of Cyclic Imines
    Chang, Mingxin
    Li, Wei
    Hou, Guohua
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3121 - 3125
  • [5] Iridium-catalyzed enantioselective hydrogenation of vinyl boronates
    Paptchikhine, Alexander
    Cheruku, Pradeep
    Engman, Mattias
    Andersson, Pher G.
    CHEMICAL COMMUNICATIONS, 2009, (40) : 5996 - 5998
  • [6] Iridium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted Nitroalkenes
    Liu, Man
    Kong, Duanyang
    Li, Meina
    Zi, Guofu
    Hou, Guohua
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) : 3875 - 3879
  • [7] Iridium-Catalyzed Enantioselective Hydrogenation of Alkenylboronic Esters
    Ganic, Adnan
    Pfaltz, Andreas
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (22) : 6724 - 6728
  • [8] Enantioselective iridium-catalyzed hydrogenation of β,β-disubstituted nitroalkenes
    Yu, Yan-Bo
    Cheng, Lei
    Li, Yi-Pan
    Fu, Yue
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    CHEMICAL COMMUNICATIONS, 2016, 52 (26) : 4812 - 4815
  • [9] Iridium-catalyzed enantioselective hydrogenation of α,β-unsaturated carboxylic acids
    Li, Shen
    Zhu, Shou-Fei
    Zhang, Can-Ming
    Song, Song
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8584 - +
  • [10] First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates
    Li, Shengkun
    Xiao, Taifeng
    Li, Dangdang
    Zhang, Xumu
    ORGANIC LETTERS, 2015, 17 (15) : 3782 - 3785