Dual Catalysis for the Redox Annulation of Nitroalkynes with Indoles: Enantioselective Construction of Indolin-3-ones Bearing Quaternary Stereocenters

被引:112
|
作者
Liu, Ren-Rong [1 ]
Ye, Shi-Chun [1 ]
Lu, Chuan-Jun [1 ]
Zhuang, Gui-Lin [1 ]
Gao, Jian-Rong [1 ]
Jia, Yi-Xia [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
关键词
asymmetric catalysis; carbenoids; chiral phosphoric acids; gold; indolinones; FRIEDEL-CRAFTS ALKYLATION; H INSERTION REACTION; OXO GOLD CARBENES; N-O BOND; RELAY CATALYSIS; 3-COMPONENT REACTIONS; CYCLIZATION; ISATOGENS; METAL; FUNCTIONALIZATION;
D O I
10.1002/anie.201504697
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The enantioselective redox annulation of nitro-alkynes with indoles is enabled by gold/chiral phosphoric acid dual catalysis. A range of indolin-3-one derivatives bearing quaternary stereocenters at the C2 position were afforded in good yields and excellent enantioselectivities (up to 96% ee) from readily available starting materials.
引用
收藏
页码:11205 / 11208
页数:4
相关论文
共 25 条
  • [1] Copper-Catalyzed Radical Difluoroalkylation and Redox Annulation of Nitroalkynes for the Construction of C2-Tetrasubstituted Indolin-3-ones
    Fu, Wenqiang
    Song, Qiuling
    ORGANIC LETTERS, 2018, 20 (02) : 393 - 396
  • [2] Enantioselective construction of dihydropyranone-fused indoles by [3+3] annulation of in situ-derived indolin-3-ones and unsaturated carboxylic esters
    Wang, Hongling
    Zhang, Qiangqiang
    Xiao, Shuai
    Wang, Guanjie
    Huang, Xuan
    Chen, Xingkuan
    Zhang, Junmin
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11): : 2740 - 2745
  • [3] Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones
    Lu, Fo-Yun
    Chen, Yu-Jue
    Chen, Yuan
    Ding, Xuan
    Guan, Zhi
    He, Yan-Hong
    CHEMICAL COMMUNICATIONS, 2020, 56 (04) : 623 - 626
  • [4] Ruthenium-Catalyzed Oxidative Dearomatization of Indoles for the Construction of C2-Quaternary Indolin-3-ones
    Zhou, Xiao-Yu
    Chen, Xia
    Wang, Liang-Guang
    Yang, Dan
    Li, Jin-Hui
    SYNLETT, 2018, 29 (06) : 835 - 839
  • [5] N-Heterocyclic Carbene-Catalyzed Enantioselective Annulation of Indolin-3-ones with Bromoenals
    Ni, Qijian
    Song, Xiaoxiao
    Raabe, Gerhard
    Enders, Dieter
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (06) : 1535 - 1538
  • [6] Copper/Diboron-Mediated Intramolecular Oxygenation and Allylation/Benzylation of Nitroalkynes for the Synthesis of C2-Quaternary Indolin-3-ones
    Fu, Wenqiang
    Zhou, Yao
    Song, Qiuling
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2511 - 2515
  • [7] Organocatalytic Asymmetric Dearomative Oxyalkylation of Indoles Enables Access to C2-Quaternary Indolin-3-ones
    Liu, Xigong
    Yan, Xue
    Yu, Jin-Hai
    Tang, Ying-De
    Wang, Kaiming
    Zhang, Hua
    ORGANIC LETTERS, 2019, 21 (14) : 5626 - 5629
  • [8] Construction of C2-Spirocyclopropyl-Indolin-3-Ones through Base-Promoted [2+1] Annulation Reaction of Indolin-3-ones with Bromosulfonium Salts
    Zhang, Mao
    Yang, Fenfen
    Guan, Xiang
    Shuai, Mingshan
    Zhang, Qingqing
    Fu, Xiaozhong
    Yang, Yuanyong
    Zhou, Meng
    He, Bin
    Zhao, Yonglong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (15)
  • [9] Asymmetric Synthesis of C2-Quaternary Indolin-3-ones Enabled by N-Heterocyclic Carbene Catalysis
    Fang, Shuaishuai
    Jin, Shiyi
    Ma, Rui
    Lu, Tao
    Du, Ding
    ORGANIC LETTERS, 2019, 21 (13) : 5211 - 5214
  • [10] Gold/Chiral Amine Relay Catalysis Enables Asymmetric Synthesis of C2-Quaternary Indolin-3-ones
    Wang, Wen-Bin
    Lu, Ji-Chao
    Bai, Hao
    Fu, Yan-Ming
    Cheng, Lan-Jun
    Zhu, Cheng-Feng
    Li, You-Gui
    Wu, Xiang
    ORGANIC LETTERS, 2024, 26 (09) : 1792 - 1796