Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel-Crafts reaction of indoles with β,β-disubstituted nitroalkenes

被引：75
|
作者：
Mori, Keiji [1 ]
Wakazawa, Manari [1 ]
Akiyama, Takahiko [1 ]
机构：
[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
来源：
CHEMICAL SCIENCE | 2014年 / 5卷 / 05期
关键词：
ORGANOCATALYTIC MICHAEL ADDITION; BOND-FORMING REACTIONS; MANNICH-TYPE REACTION; BRONSTED ACID; CONJUGATE ADDITION; STEREOGENIC CENTERS; ISATYLIDENE-3-ACETALDEHYDES APPLICATION; 1,3-DIPOLAR CYCLOADDITION; EFFICIENT ORGANOCATALYSTS; 1,4-ADDITION REACTIONS;
D O I：
10.1039/c3sc53542h
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We describe herein a chiral phosphoric acid catalyzed Friedel-Crafts reaction of indoles with beta-alkoxycarbonyl-beta-disubstituted nitroalkenes. A wide variety of substrates participated in this reaction to afford indoles having all-carbon quaternary centers with excellent selectivities ( up to 97% ee). Further investigation suggested that the olefin geometry and the employment of NH-indole derivatives are responsible for both reactivity and selectivity.
引用
收藏
页码：1799 / 1803
页数：5
相关论文
共 50 条
  • [1] Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid
    Kang, Qiang
    Zhao, Zhuo-An
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) : 1484 - +
  • [2] The Asymmetric Friedel-Crafts Reaction of Indoles with Fluoroalkylated Nitroalkenes Catalyzed by Chiral Phosphoric Acid
    Lin, Jin-Hong
    Xiao, Ji-Chang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (24) : 4536 - 4539
  • [3] Chiral Bronsted acid catalyzed intermolecular Friedel-Crafts alkylation of styrenes with indoles: construction of all-carbon quaternary stereocenters
    Li, Ming-Li
    Chen, Dian-Feng
    Luo, Shi-Wei
    Wu, Xiang
    TETRAHEDRON-ASYMMETRY, 2015, 26 (04) : 219 - 224
  • [4] Construction of Chiral All-Carbon Quaternary Stereocenters by Asymmetric Friedel-Crafts Reaction of Isatin Derivatives
    Li, Jindong
    Lu, Wenjing
    Lu, Yangmian
    Zha, Zhenggen
    Wang, Zhiyong
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (02) : 195 - 200
  • [5] Chiral bronsted acid catalyzed enantioselective Friedel-Crafts reaction of indoles and α-aryl enamides:: Construction of quaternary carbon atoms
    Jia, Yi-Xia
    Zhong, Jun
    Zhu, Shou-Fei
    Zhang, Can-Ming
    Zhou, Qi-Lin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5565 - 5567
  • [6] Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation Reaction
    Gao, Jian-Rong
    Wu, Hao
    Xiang, Bin
    Yu, Wu-Bin
    Han, Liang
    Jia, Yi-Xia
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) : 2983 - 2986
  • [7] Chiral Calcium Phosphate Catalyzed Enantioselective Synthesis of All-Carbon Quaternary Center by Friedel-Crafts Alkylation Reaction of Pyrroles and Trifluoromethylated Nitrostyrenes
    Uchikura, Tatsuhiro
    Yokohama, Sosuke
    Murakami, Mona
    Akiyama, Takahiko
    SYNTHESIS-STUTTGART, 2022, 54 (17): : 3793 - 3800
  • [8] Chiral phosphoric acid catalyzed enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes:: Cooperative effect of 3 Å molecular sieves
    Itoh, Junji
    Fuchibe, Kohei
    Akiyama, Takahiko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (21) : 4016 - 4018
  • [9] Asymmmetric Friedel-Crafts Alkylation Reaction in the Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters
    Wu, Hao
    Liu, Ren-Rong
    Jia, Yi-Xia
    SYNLETT, 2014, 25 (04) : 457 - 460
  • [10] Enantioselective Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid
    Bachu, Prabhakar
    Akiyama, Takahiko
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4112 - 4114
12345