Squaramide-catalyzed enantioselective Friedel-Crafts reaction of indoles with imines

被引：163
|
作者：
Qian, Yong [1 ]
Ma, Gaoyuan [1 ]
Lv, Aifeng [1 ]
Zhu, Hai-Liang [1 ]
Zhao, Jing [1 ,2 ]
Rawal, Viresh H. [3 ]
机构：
[1] Nanjing Univ, State Key Lab Pharmaceut Biotechnol, Sch Life Sci, Nanjing 210008, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
[3] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
来源：
CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 17期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
CHIRAL PHOSPHORIC-ACID; ASYMMETRIC CATALYSIS; BRONSTED ACID; ALKYLATION; DERIVATIVES; NITROALKENES; DONORS;
D O I：
10.1039/b922120d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral squaramides are highly enantioselective catalysts for Friedel-Crafts reaction of indoles with N-tosyl imines, affording 3-indolyl methanamine products in 85-96% yields and 84-96% ees.
引用
收藏
页码：3004 / 3006
页数：3
相关论文
共 50 条
  • [31] Regio- and Enantioselective Friedel-Crafts Reactions of Indoles to Epoxides Catalyzed by Graphene Oxide: A Green Approach
    Acocella, Maria Rosaria
    Mauro, Marco
    Guerra, Gaetano
    CHEMSUSCHEM, 2014, 7 (12) : 3279 - 3283
  • [32] Chiral Bronsted Acid Directed Iron-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with β-Aryl α′-Hydroxy Enones
    Yang, Lei
    Zhu, Qiming
    Guo, Shengmei
    Qian, Bo
    Xia, Chungu
    Huang, Hanmin
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1638 - 1645
  • [33] Friedel-Crafts alkylation of indoles with trichloroacetimidates
    Suzuki, Tamie
    Chisholm, John D.
    TETRAHEDRON LETTERS, 2019, 60 (19) : 1325 - 1329
  • [34] Enantioselective Synthesis of Fluorene Derivatives by Chiral Phosphoric Acid Catalyzed Tandem Double Friedel-Crafts Reaction
    Sun, Feng-Lai
    Zeng, Mi
    Gu, Qing
    You, Shu-Li
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (35) : 8709 - 8712
  • [35] Chiral phosphoric acid-catalyzed enantioselective Aza-Friedel-Crafts reaction of Indoles
    Terada, Masahiro
    Yokoyama, Shigeko
    Sorimachi, Keiichi
    Uraguchi, Daisuke
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (11-12) : 1863 - 1867
  • [36] An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
    Hong, Liang
    Wang, Lei
    Chen, Chao
    Zhang, Bangzhi
    Wang, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 772 - 778
  • [37] Research Progress in Friedel-Crafts Reaction of Indoles and Nitroalkenes
    Wang, Chunchao
    Xie, Shaolei
    Xie, Zhengfeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (09) : 1919 - 1931
  • [38] Enantioselective Friedel-Crafts alkylation of indole with nitroalkenes in the presence of bifunctional squaramide organocatalysts
    Dundar, Esra
    Tanyeli, Cihangir
    TETRAHEDRON LETTERS, 2021, 73
  • [39] 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
  • [40] Friedel-Crafts Reaction of Indoles with N-Sulfonyl Imines Catalyzed by H3PW12O40
    Hui, Yonghai
    Wang, Changchun
    Shi, Wei
    Meng, Hua
    Xie, Zhengfeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (05) : 898 - 902
12345