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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 17期
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
  • [41] ORGN 166-Bicyclic guanidine-catalyzed enantioselective phospha-Michael reactions
    Fu, Xiao
    Tan, Choon-Hong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [42] Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex
    Takita, Ryo
    Yakura, Kenichiro
    Ohshima, Takashi
    Shibasaki, Masakatsu
    Journal of the American Chemical Society, 2005, 127 (40): : 13760 - 13761
  • [43] Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex
    Takita, R
    Yakura, K
    Ohshima, T
    Shibasaki, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) : 13760 - 13761
  • [44] Rhodium-catalyzed asymmetric conjugate alkynylation of nitroalkenes
    Nishimura, Takahiro
    Sawano, Takahiro
    Tokuji, Sumito
    Hayashi, Tamio
    CHEMICAL COMMUNICATIONS, 2010, 46 (36) : 6837 - 6839
  • [45] Kinetic Resolution of Oxaziridines via Chiral Bifunctional Guanidine-Catalyzed Enantioselective α-Hydroxylation of β-Keto Esters
    Lin, Xiaobin
    Ruan, Sai
    Yao, Qian
    Yin, Chengkai
    Lin, Lili
    Feng, Xiaoming
    Liu, Xiaohua
    ORGANIC LETTERS, 2016, 18 (15) : 3602 - 3605
  • [46] Origin of Asymmetric Induction in Bicyclic Guanidine-Catalyzed Thio-Michael Reaction: A Bifunctional Mode of Lewis Acid-Bronsted Acid Activation
    Cho, Bokun
    Tan, Choon-Hong
    Wong, Ming Wah
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15): : 6553 - 6562
  • [47] Asymmetric Alkynylation of Tertiary Carbon-Centered Radical via Copper-Catalyzed Radical Relay
    Wu, Dunqi
    Wu, Lianqian
    Chen, Pinhong
    Liu, Guosheng
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (14) : 1699 - 1704
  • [48] Copper-Catalyzed Asymmetric Deconstructive Alkynylation of Cyclic Oximes (vol 11, pg 6010, 2021)
    Zuo, Hang-Dong
    Zhu, Shan-Shan
    Hao, Wen-Juan
    Wang, Shi-Chao
    Tu, Shu-Jiang
    Jiang, Bo
    ACS CATALYSIS, 2021, 11 (12): : 7310 - 7310
  • [49] Enantioselective copper-catalyzed alkynylation of chromene acetals
    Srinivas, Harathi D.
    Maity, Prantik
    Watson, Mary P.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [50] Asymmetric aldol reactions of isatins catalyzed by phthalimido-prolinamide
    Kumar, Togapur Pavan
    Manjula, Nemali
    Katragunta, Kumar
    TETRAHEDRON-ASYMMETRY, 2015, 26 (21-22) : 1281 - 1284
12345