Chiral Bronsted acid catalyzed intermolecular Friedel-Crafts alkylation of styrenes with indoles: construction of all-carbon quaternary stereocenters

被引:33
作者
Li, Ming-Li
Chen, Dian-Feng
Luo, Shi-Wei
Wu, Xiang [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
ORTHO-QUINONE METHIDES; ENANTIOSELECTIVE CONSTRUCTION; ORGANOCATALYTIC CHEMO; ASYMMETRIC-SYNTHESIS; FUNCTIONALIZATION; ACTIVATION; CENTERS;
D O I
10.1016/j.tetasy.2015.01.005
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A chiral Bronsted acid catalyzed Friedel-Crafts reaction of terminal 1,1-diaryalkenes with indoles is described. This reaction provides indole derivatives with acyclic all-carbon quaternary stereocenters in excellent yields and with excellent enantioselectivities, and features high atom efficiency without the generation of side products. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:219 / 224
页数:6
相关论文
共 52 条
  • [1] Adair G, 2008, ALDRICHIM ACTA, V41, P31
  • [2] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [3] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction
    Bandini, M
    Melloni, A
    Umani-Ronchi, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) : 550 - 556
  • [4] Bandini M., 2009, Catalytic Asymmetric Friedel-Crafts Alkylations
  • [5] Catalytic Functionalization of Indoles in a New Dimension
    Bandini, Marco
    Eichholzer, Astrid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
  • [6] Organocatalytic Formation of Quaternary Stereocenters
    Bella, Marco
    Gasperi, Tecla
    [J]. SYNTHESIS-STUTTGART, 2009, (10): : 1583 - 1614
  • [7] Synthesis and functionalization of Indoles through palladium-catalyzed reactions
    Cacchi, S
    Fabrizi, G
    [J]. CHEMICAL REVIEWS, 2005, 105 (07) : 2873 - 2920
  • [8] Catalytic functionalization of tertiary alcohols to fully substituted carbon centres
    Chen, Long
    Yin, Xiao-Ping
    Wang, Cui-Hong
    Zhou, Jian
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (32) : 6033 - 6048
  • [9] Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858
  • [10] Christoffers J, 2001, ANGEW CHEM INT EDIT, V40, P4591, DOI 10.1002/1521-3773(20011217)40:24<4591::AID-ANIE4591>3.0.CO