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 95 条
  • [1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
    Anand, NK
    Carreira, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) : 9687 - 9688
  • [2] [Anonymous], 2009, ANGEW CHEM
  • [3] Alkoxide-catalyzed addition of terminal alkynes to ketones
    Babler, JH
    Liptak, VP
    Phan, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 416 - 417
  • [4] Cu(II)-Cu(I) Synergistic Cooperation to Lead the Alkyne C-H Activation
    Bai, Ruopeng
    Zhang, Guanghui
    Yi, Hong
    Huang, Zhiliang
    Qi, Xiaotian
    Liu, Chao
    Miller, Jeffrey T.
    Kropf, A. Jeremy
    Bunel, Emilio E.
    Lan, Yu
    Lei, Aiwen
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (48) : 16760 - 16763
  • [5] The coordination chemistry of guanidines and guanidinates
    Bailey, PJ
    Pace, S
    [J]. COORDINATION CHEMISTRY REVIEWS, 2001, 214 : 91 - 141
  • [6] Design, synthesis and pharmacological evaluation of HIV-1 reverse transcriptase inhibition of new indolin-2-ones
    Boechat, Nubia
    Kover, W. Bruce
    Bongertz, Vera
    Bastos, Monica M.
    Romeiro, Nelilma C.
    Azevedo, Maria L. G.
    Wollinger, Wagner
    [J]. MEDICINAL CHEMISTRY, 2007, 3 (06) : 533 - 542
  • [7] Camphor-based Schiff base ligand SBAIB: an enantioselective catalyst for addition of phenylacetylene to aldehydes
    Boobalan, Ramalingam
    Chen, Chinpiao
    Lee, Gene-Hsian
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (08) : 1625 - 1638
  • [8] Chang K. H., 2004, ANGEW CHEM, P1731
  • [9] Low ligand loading, highly enantioselective addition of phenylacetylene to aromatic ketones catalyzed by Schiff-base amino alcohols
    Chen, Chao
    Hong, Liang
    Xu, Zhao-Qing
    Liu, Lei
    Wang, Rui
    [J]. ORGANIC LETTERS, 2006, 8 (11) : 2277 - 2280
  • [10] Synthesis and Bioactivity Evaluation of 3-Hydroxy-3-(phenylethynyl)indol-2-one Analogues
    Chen, Gang
    Wang, Ye
    Gao, Suo
    He, Hong-Ping
    Li, Shun-Lin
    Zhang, Jian-Xin
    Ding, Jian
    Hoa, Xiao-Jiang
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (02) : 217 - 220
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