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
  • [21] Highly Enantioselective Friedel-Crafts Reactions of Indoles with Isatins Catalyzed by Chiral Imidodiphosphoric Acids
    Liu, Guofeng
    Zhuo, Minghua
    An, Dong
    Zhang, Guangliang
    Qin, Xiangshuo
    Gao, Jigang
    Fan, Yansen
    Zhang, Suoqin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 807 - 811
  • [22] Enantioselective Friedel-Crafts Reaction of Indoles with N-Tosylimines Employing Takemoto's Organocatalyst
    Wang, Liming
    Wu, Hao
    Ding, Ruxin
    Chen, Zhe
    Jin, Ying
    CURRENT ORGANIC CHEMISTRY, 2019, 23 (15) : 1688 - 1694
  • [23] Enantioselective Friedel-Crafts Alkylation of Furans and Indoles with Simple α,β-Unsaturated Ketones Catalyzed by Oxazaborolidinone
    Adachi, Shinya
    Tanaka, Fumi
    Watanabe, Kazuya
    Watada, Atsushi
    Harada, Toshiro
    SYNTHESIS-STUTTGART, 2010, (15): : 2652 - 2669
  • [24] Highly Enantioselective Zinc-Catalyzed Friedel-Crafts Alkylation of Indoles with Ethyl Trifluoropyruvate
    Hui, Yonghai
    Chen, Weiliang
    Wang, Wentao
    Jiang, Jun
    Cai, Yunfei
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) : 3174 - 3178
  • [25] Porous Carbon Nanosheet-Supported Chiral Squaramide for Highly Enantioselective Friedel-Crafts Reaction
    Zhao, Liyuan
    Bao, Xiaoze
    Hu, Qingtao
    Wang, Baomin
    Lu, An-Hui
    CHEMCATCHEM, 2018, 10 (06) : 1248 - 1252
  • [26] Organocatalytic Enantioselective Friedel-Crafts Reaction of Sesamol and Electron-rich Phenols with Alkylideneindolenine Intermediates Generated from Arylsulfonyl Indoles
    Chang, Chia-Hao
    Han, Jeng-Liang
    CHEMISTRYSELECT, 2016, 1 (18): : 5628 - 5632
  • [27] CHIRAL PHOSPHORIC ACID CATALYZED ASYMMETRIC FRIEDEL-CRAFTS ALKYLATION OF INDOLES WITH NITROOLEFINS
    Tang, Hong-Ying
    Zhang, Zhong-Biao
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (10) : 2038 - 2046
  • [28] BrOnsted Acid-Catalyzed Friedel-Crafts Reaction of Indoles to -Ketimino Esters
    Yang, Jin-Hui
    Lou, Qin-Xin
    Chen, Yan-Xue
    Tang, Kang-Kang
    SYNTHETIC COMMUNICATIONS, 2015, 45 (16) : 1887 - 1892
  • [29] Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
    Montesinos-Magraner, Marc
    Vila, Carlos
    Rendon-Patino, Alejandra
    Blay, Gonzalo
    Fernandez, Isabel
    Munoz, M. Carmen
    Pedro, Jose R.
    ACS CATALYSIS, 2016, 6 (04): : 2689 - 2693
  • [30] Enantioselective synthesis of quaternary α-aminophosphonates by organocatalytic Friedel-Crafts reactions of indoles with cyclic α-ketiminophosphonates
    Yan, Zhong
    Gao, Xiang
    Zhou, Yong-Gui
    CHINESE JOURNAL OF CATALYSIS, 2017, 38 (05) : 784 - 792
12345