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
  • [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] Double Axially Chiral Bisphosphorylimides Catalyzed Highly Enantioselective and Efficient Friedel-Crafts Reaction of Indoles with Imines
    Wu, Kun
    Jiang, Yi-Jun
    Fan, Yan-Sen
    Sha, Di
    Zhang, Suoqin
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (02) : 473 - 477
  • [3] Enantioselective Friedel-Crafts Reaction of Indoles with Trifluoroacetaldehyde Catalyzed by Cinchona Alkaloids
    Borkin, Dmitry A.
    Landge, Shainaz M.
    Toeroek, Bela
    CHIRALITY, 2011, 23 (08) : 612 - 616
  • [4] Research Progress in Friedel-Crafts Reaction of Indoles and Imines
    Chen, Yongcheng
    Xie, Zhengfeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (03) : 462 - 471
  • [5] Organocatalytic Enantioselective Friedel-Crafts Reaction of Phenanthrenequinones and Indoles
    Jin, Yan
    Sun, Yuhong
    Yu, Yue
    Zhao, Jiao
    Zheng, Mingshan
    Wang, Liming
    Jin, Ying
    MOLECULES, 2025, 30 (01):
  • [6] Enantioselective Friedel-Crafts reaction with indoles and ethyl trifluoropyruvate
    Zhang, Peng
    Wolf, Christian
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [7] Asymmetric Friedel-Crafts reaction of indoles with imines by an organic catalyst
    Wang, Yong-Qiang
    Song, Jun
    Hong, Ran
    Li, Hongming
    Deng, Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) : 8156 - 8157
  • [8] Enantioselective Friedel-Crafts reaction of indoles with carbonyl compounds catalyzed by bifunctional cinchona alkaloids
    Li, Hongming
    Wang, Yong-Qiang
    Deng, Li
    ORGANIC LETTERS, 2006, 8 (18) : 4063 - 4065
  • [9] Organocatalytic enantioselective Friedel-Crafts reaction of pyrrole derivatives with imines
    Li, Guilong
    Rowland, Gerald B.
    Rowland, Emily B.
    Antilla, Jon C.
    ORGANIC LETTERS, 2007, 9 (20) : 4065 - 4068
  • [10] SPINOL-Derived Phosphoric Acids: Synthesis and Application in Enantioselective Friedel-Crafts Reaction of Indoles with Imines
    Xu, Fangxi
    Huang, Dan
    Han, Chao
    Shen, Wei
    Lin, Xufeng
    Wang, Yanguang
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24): : 8677 - 8680
12345