Copper/Guanidine-Catalyzed Asymmetric Alkynylation of Isatins

被引:100
|
作者
Chen, Quangang [1 ]
Tang, Yu [1 ]
Huang, Tianyu [1 ]
Liu, Xiaohua [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ,2 ]
机构
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
基金
中国国家自然科学基金;
关键词
alkynes; asymmetric catalysis; copper; heterocycles; ligand design; HIGHLY ENANTIOSELECTIVE ADDITION; AROMATIC-ALDEHYDES; TERMINAL ALKYNES; PROPARGYLIC ALCOHOLS; TRIFLUOROMETHYL KETONES; COORDINATION CHEMISTRY; CONVENIENT SYNTHESIS; TITANIUM COMPLEX; CARBONYL GROUPS; H INSERTION;
D O I
10.1002/anie.201600711
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The highly enantioselective alkynylation of isatins, catalyzed by a bifunctional guanidine/CuI catalyst under mild reaction conditions, is described. The reaction is broad in scope with respect to alkyl/aryl-substituted terminal alkynes and substituted isatins, thus affording bioactive propargylic alcohols in excellent yields and enantioselectivities.
引用
收藏
页码:5286 / 5289
页数:4
相关论文
共 50 条
  • [21] Cooperative Chiral Guanidine/AgPF6 Catalyzed Asymmetric Isocyanoacetate Aldol Reaction with Isatins
    Lu, Yan
    Wang, Min
    Zhao, Xiaohu
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    SYNLETT, 2015, 26 (11) : 1545 - 1548
  • [22] Bicyclic Guanidine-Catalyzed Direct Asymmetric Allylic Addition of N-Aryl Alkylidene-Succinimides
    Wang, Jianmin
    Liu, Hongjun
    Fan, Yitian
    Yang, Yuanyong
    Jiang, Zhiyong
    Tan, Choon-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) : 12534 - 12537
  • [23] Photoinduced Copper-Catalyzed Asymmetric Decarboxylative Alkynylation with Terminal Alkynes
    Xia, Hai-Dong
    Li, Zhong-Liang
    Gu, Qiang-Shuai
    Dong, Xiao-Yang
    Fang, Jia-Heng
    Du, Xuan-Yi
    Wang, Li-Lei
    Liu, Xin-Yuan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (39) : 16926 - 16932
  • [24] Mechanistic Study of Asymmetric Alkynylation of Isatin-Derived Ketimine Mediated by a Copper/Guanidine Catalyst
    Zhang, Yan
    Lv, Cidan
    Hu, Changwei
    Su, Zhishan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (17): : 11693 - 11707
  • [25] Bicyclic guanidine-catalyzed asymmetric Michael additions of 3-benzyl-substituted oxindoles to N-maleimides
    Li, Lixin
    Chen, Wenchao
    Yang, Wenguo
    Pan, Yuanhang
    Liu, Hongjun
    Tan, Choon-Hong
    Jiang, Zhiyong
    CHEMICAL COMMUNICATIONS, 2012, 48 (42) : 5124 - 5126
  • [26] Efficient Guanidine-Catalyzed Alkylation of Indoles with Fluoromethyl Ketones in the presence of Water
    Bandini, Marco
    Sinisi, Riccardo
    ORGANIC LETTERS, 2009, 11 (10) : 2093 - 2096
  • [27] Copper-catalyzed asymmetric alkynylation of cyclic N-sulfonyl ketimines
    Ling, Zheng
    Singh, Sonia
    Xie, Fang
    Wu, Liang
    Zhang, Wanbin
    CHEMICAL COMMUNICATIONS, 2017, 53 (39) : 5364 - 5367
  • [28] Access to the nicotine system by application of a guanidine-catalyzed asymmetric Michael addition of diphenyliminoacetate with 3-pyridyl vinyl ketone
    Zhang, Gang
    Kumamoto, Takuya
    Heima, Takashi
    Ishikawa, Tsutomu
    TETRAHEDRON LETTERS, 2010, 51 (30) : 3927 - 3930
  • [29] Density functional study on the mechanism of bicyclic guanidine-catalyzed Strecker reaction
    Li, J
    Jiang, WY
    Han, KL
    He, GZ
    Li, C
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 8786 - 8789
  • [30] Rate Acceleration of Triethylamine-Mediated Guanidine-Catalyzed Enantioselective Michael Reaction
    Jiang, Zhiyong
    Ye, Weiping
    Yang, Yuanyong
    Tan, Choon-Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (14-15) : 2345 - 2351