Enantioselective Synthesis of Unsymmetrical Triarylmethanes by Chiral Bronsted Acids

被引:153
|
作者
Sun, Feng-Lai [1 ]
Zheng, Xiao-Jian [1 ]
Gu, Qing [1 ]
He, Qing-Li [1 ]
You, Shu-Li [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Chiral Bronsted acids; Enantioselectivity; Friedel-Crafts reaction; Indole; Organocatalysis; FRIEDEL-CRAFTS REACTION; ELECTRON-RICH ARENES; ARYLBORONIC ACIDS; PHOSPHORIC-ACIDS; ALKYLATION; INDOLES; IMINES; DERIVATIVES; CATALYST; ACCESS;
D O I
10.1002/ejoc.200901164
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral Bronsted acid catalyzed Friedel-Crafts alkylation of electron-rich arenes with (3-indolyl)methanamines has been realized to provide an efficient synthesis of enantioenriched unsymmetrical triarylmethanes. With 5 mol-% of a newly developed chiral phosphoric acid, the enantioenriched unsymmetrical triarylmethanes were obtained in excellent yields with up to 91 % ee.
引用
收藏
页码:47 / 50
页数:4
相关论文
共 50 条
  • [31] Chiral Bronsted Acid Catalyzed Enantioselective α-Aminoxylation of Enecarbamates
    Zhong, Guofu
    Lu, Min
    SYNTHESIS-STUTTGART, 2011, (03): : A13 - A14
  • [32] A new chiral catalyst for the enantioselective Strecker synthesis of α-amino acids
    Huang, JK
    Corey, EJ
    ORGANIC LETTERS, 2004, 6 (26) : 5027 - 5029
  • [34] N -Triflylphosphorimidoyl Trichloride: A Versatile Reagent for the Synthesis of Strong Chiral BrOnsted Acids
    Lee, Sunggi
    Kaib, Philip S. J.
    List, Benjamin
    SYNLETT, 2017, 28 (12) : 1478 - 1480
  • [35] Synthesis of Chiral Unnatural α-Amino Acids Enabled by Photoredox/Bronsted Acid Cocatalysis
    Zhang, Hong-Hao
    Yu, Shouyun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1744 - 1745
  • [36] Synthesis of unsymmetrical chiral salens
    Burd, Caroline
    Holbach, Michael
    Zheng, Xiaolai
    Jones, Christopher W.
    Weck, Marcus
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [37] Asymmetric reactions catalyzed by chiral Bronsted acids
    Kano, Taichi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2006, 64 (10) : 1075 - 1076
  • [38] NOVEL STEROIDAL CHIRAL AUXILIARIES - ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS
    HUANG, DL
    DRAPER, RW
    TETRAHEDRON LETTERS, 1994, 35 (05) : 661 - 662
  • [39] Synthesis of novel chiral fluorescent sensors and their application in enantioselective discrimination of chiral carboxylic acids
    Yu, Qiuhan
    Lu, Weiwen
    Ding, Zhigiang
    Wei, Min
    Dai, Zhenya
    JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (9-10) : 340 - 346
  • [40] Chiral Bronsted Acid Catalyzed Enantioselective Propargylation of Aldehydes with Allenylboronate
    Reddy, Leleti Rajender
    ORGANIC LETTERS, 2012, 14 (04) : 1142 - 1145