Ir-catalyzed asymmetric hydrogenation of 2-Aryl-3H-indoles with chiral phosphine-phosphoramidite ligands

被引:1
|
作者
Cao, Haiyan [1 ]
Zhou, Mingdong [1 ]
Yin, Hang [1 ]
Zheng, Kaikai [1 ]
Zhang, Zheng [1 ]
Shuai, Qiucen [1 ]
Guan, Ruitong [1 ]
Wang, Kangjun [1 ]
Yang, Ying [1 ]
Guan, Jin [1 ]
Hu, Xinhu [1 ]
机构
[1] Shenyang Univ Chem Technol, Coll Chem Engn, Shenyang 110142, Peoples R China
关键词
Hydrogenation; Asymmetric catalysis; Iridium; 2-Aryl-3H-indoles; Chiral phosphine-phosphoramidite ligand; HIGHLY ENANTIOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; INDOLINES; INDOLES; ACID; DEAROMATIZATION; ALKYLATION; DIVERSITY; COMPLEXES; SCAFFOLDS;
D O I
10.1016/j.jorganchem.2023.122953
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An asymmetric synthesis of indolines has been described by using an Ir-catalyzed asymmetric hydrogenation of 2-aryl-3H-indoles with unsymmetrical hybrid chiral phosphine-phosphoramidite ligands. The result indicated that the catalytic performance could be significantly improved by the H8-binaphthyl moiety on this ligand motif. This method is characterized by a high asymmetric induction and a reasonable functional group tolerance, thus providing a concise and efficient approach toward chiral indoline and their derivatives with up to 94 % ee.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P, N, N-ligands
    Chen, Xiu-Shuai
    Hou, Chuan-Jin
    Qin, Chao
    Liu, Hongzhu
    Liu, Yan-Jun
    Huang, De-Zhi
    Hu, Xiang-Ping
    RSC ADVANCES, 2017, 7 (21): : 12871 - 12875
  • [22] Chiral 1-Phosphabarrelene-Pyridines as Suitable Ligands for the Rh/Ir-Catalyzed Asymmetric Hydrogenation of Olefins
    Salto, Joan
    Tarr, Daniel
    Petrov, Andrey
    Reich, Dorian
    Weber, Manuela
    Biosca, Maria
    Pamies, Oscar
    Mueller, Christian
    Dieguez, Montserrat
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (04) : 813 - 821
  • [23] Spiro-Josiphos Ligands for the Ir-Catalyzed Asymmetric Synthesis of Chiral Amines under Hydrogenation Conditions
    Li, Bin
    Zhou, Gang
    Zhang, Dongxu
    Yao, Lin
    Li, Muqiong
    Yang, Guidong
    Zhang, Shengyong
    Nie, Huifang
    ORGANIC LETTERS, 2024, 26 (10) : 2097 - 2102
  • [24] Enantioselective Synthesis of Tunable Chiral Clickphine P,N-Ligands and Their Application in Ir-Catalyzed Asymmetric Hydrogenation
    Wassenaar, Jeroen
    Detz, Remko J.
    de Boer, Sandra Y.
    Lutz, Martin
    van Maarseveen, Jan H.
    Hiemstra, Henk
    Reek, Joost N. H.
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07) : 3634 - 3642
  • [25] Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
    Lyubimov, S. E.
    Ozolin, D. V.
    Davankov, V. A.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (06) : 1059 - 1061
  • [26] Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks
    Paptchikhine, Alexander
    Itto, Kaori
    Andersson, Pher G.
    CHEMICAL COMMUNICATIONS, 2011, 47 (13) : 3989 - 3991
  • [27] Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands
    S. E. Lyubimov
    D. V. Ozolin
    V. A. Davankov
    Russian Chemical Bulletin, 2017, 66 : 1059 - 1061
  • [28] Rh-catalyzed asymmetric hydrogenation of α-aryl-β-alkylvinyl esters with chiral ferrocenylphosphine-phosphoramidite ligand
    Dong, Chao
    Liu, Dao-Sheng
    Zhang, Lei
    Hu, Xiang-Ping
    TETRAHEDRON LETTERS, 2021, 65
  • [29] Well-Designed Chiral Ligands for Enantioselective Ir-Catalyzed C(sp2)-H Borylation†
    Wang, Yin-Xia
    Zhang, Ping-Feng
    Ye, Mengchun
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1762 - 1766
  • [30] Chiral 1-phenylethylamine-derived phosphine-phosphoramidite ligands for highly enantioselective Rh-catalyzed hydrogenation of β-(acylamino)acrylates: significant effect of substituents on 3,3′-positions of binaphthyl moiety
    Zhou, Xiao-Mao
    Huang, Jia-Di
    Luo, Li-Bin
    Zhang, Chen-Lu
    Hu, Xiang-Ping
    Zheng, Zhuo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (10) : 2320 - 2322