Enantioselective synthesis of fluorene derivatives by chiral N-triflyl phosphoramide catalyzed double Friedel-Crafts alkylation reaction

被引：44
|
作者：
Wang, Shou-Guo [1 ]
Han, Long [1 ]
Zeng, Mi [1 ]
Sun, Feng-Lai [1 ]
Zhang, Wei [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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 16期
基金：
中国国家自然科学基金;
关键词：
BRONSTED ACID; INDOLES; CONSTRUCTION; 4,7-DIHYDROINDOLES; ACTIVATION; ENAMIDES; DESIGN; IMINES; MOTIF;
D O I：
10.1039/c2ob07168a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient tandem double Friedel-Crafts reaction between indoles and 2-formylbiphenyl derivatives by chiral N-triflyl phosphoramide was realized. Under mild conditions, various 9-(3-indolyl)fluorene derivatives have been obtained in good yield and up to 94% ee. Comparing to their corresponding chiral phosphoric acids, chiral N-triflyl phosphoramides catalyzed reactions led to products with opposite absolute configuration.
引用
收藏
页码：3202 / 3209
页数：8
相关论文
共 50 条
  • [1] Enantioselective Synthesis of Tetrahydropyrano[3,4-b]indoles Catalyzed by Chiral N-Triflyl Phosphoramide via Intramolecular Friedel-Crafts Alkylation Reaction
    Zhang, Jun-Wei
    Cai, Quan
    Shi, Xiao-Xin
    Zhang, Wei
    You, Shu-Li
    SYNLETT, 2011, (09) : 1239 - 1242
  • [2] 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
  • [3] One-Pot Synthesis of Pyrrolo[1,2-a]indoles by Chiral N-Triflyl Phosphoramide Catalyzed Friedel-Crafts Alkylation of 4,7-Dihydroindole with β,γ-Unsaturated α-Keto Esters
    Zeng Mi
    Zhang Wei
    You Shuli
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (11) : 2615 - 2623
  • [4] Synthesis of Fluorene Derivatives Via TfOH-catalyzed Intramolecular Friedel-Crafts Alkylation Reactions
    Zhou, Ziyang
    Yi, Ying
    Zhang, Fanglin
    Xu, Wengang
    Lu, Zhi
    Luo, Tian
    JOURNAL OF WUHAN UNIVERSITY OF TECHNOLOGY-MATERIALS SCIENCE EDITION, 2023, 38 (05): : 1184 - 1189
  • [5] Synthesis of Fluorene Derivatives Via TfOH-catalyzed Intramolecular Friedel-Crafts Alkylation Reactions
    Ziyang Zhou
    Ying Yi
    Fanglin Zhang
    Wengang Xu
    Zhi Lu
    Tian Luo
    Journal of Wuhan University of Technology-Mater. Sci. Ed., 2023, 38 : 1184 - 1189
  • [6] Synthesis of Fluorene Derivatives Via TfOH-catalyzed Intramolecular Friedel-Crafts Alkylation Reactions
    周子杨
    易英
    ZHANG Fanglin
    XU Wengang
    LU Zhi
    LUO Tian
    JournalofWuhanUniversityofTechnology(MaterialsScience), 2023, 38 (05) : 1184 - 1189
  • [7] 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
  • [8] Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate
    Ibanez, Ignacio
    Kaneko, Mio
    Kamei, Yuto
    Tsutsumi, Ryosuke
    Yamanaka, Masahiro
    Akiyama, Takahiko
    ACS CATALYSIS, 2019, 9 (08) : 6903 - 6909
  • [9] Chiral Bis(Oxazolinyl)thiophenes for Enantioselective Cu(II)-Catalyzed Friedel-Crafts Alkylation of Indole Derivatives with Nitroalkenes
    Li, Weijie
    CATALYSIS LETTERS, 2014, 144 (05) : 943 - 948
  • [10] Enantioselective Friedel-Crafts alkylation for synthesis of 2-substituted indole derivatives
    Zhang, Yulong
    Liu, Xiaohua
    Zhao, Xiaohu
    Zhang, Jianlin
    Zhou, Lin
    Lin, Lili
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2013, 49 (96) : 11311 - 11313
12345