Cu(I)-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with 2-Aryl-N-sulfonylaziridines as Alkylating Agents

被引:42
|
作者
Ge, Chen [1 ]
Liu, Ren-Rong [1 ]
Gao, Jian-Rong [1 ]
Jia, Yi-Xia [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON QUATERNARY STEREOCENTERS; RING-OPENING REACTIONS; MESO-EPOXIDES; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; CONSTRUCTION; AZIRIDINES; DERIVATIVES; PYRROLOINDOLINES;
D O I
10.1021/acs.orglett.6b01317
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly enantioselective Friedel-Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu-(CH3CN)(4)BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.
引用
收藏
页码:3122 / 3125
页数:4
相关论文
共 50 条
  • [21] Enantioselective Friedel-Crafts Alkylation of Indoles with Alkylidene Malonates Catalyzed by N,N′-Dioxide-Scandium(III) Complexes: Asymmetric Synthesis of β-Carbolines
    Liu, Yanling
    Shang, Deju
    Zhou, Xin
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) : 2055 - 2058
  • [22] Friedel-Crafts Alkylation of Indoles with Aldehydes/Ketones Catalyzed by Bromodiarylethene-Based Photoacid Generators
    Zakharov, Alexey V.
    Timofeeva, Sofia M.
    Shirinian, Valerii Z.
    SYNTHESIS-STUTTGART, 2024, 56 (14): : 2247 - 2258
  • [23] Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative
    Zhang, Junwei
    Wu, Hao
    Zhang, Weixin
    Wang, Liming
    Jin, Ying
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (03) : 1187 - 1192
  • [24] 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
  • [25] Chiral phosphoric acid catalyzed enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes:: Cooperative effect of 3 Å molecular sieves
    Itoh, Junji
    Fuchibe, Kohei
    Akiyama, Takahiko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (21) : 4016 - 4018
  • [26] Asymmetric Friedel-Crafts Alkylation of Indoles with Trifluoromethyl Pyruvate Catalyzed by a Dinuclear Zinc Catalyst
    Hua, Yuan-Zhao
    Chen, Jun-Wei
    Yang, Hua
    Wang, Min-Can
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03): : 1160 - 1166
  • [27] Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Fumarate Derivatives in the Presence of Chiral Palladium Complexes
    Lee, Hyun Joo
    Kim, Dae Young
    SYNLETT, 2012, (11) : 1629 - 1632
  • [28] Highly enantioselective Friedel-Crafts alkylation of indole and pyrrole with β,γ-unsaturated α-ketoester catalyzed by chiral dicationic palladium complex
    Aikawa, Kohsuke
    Honda, Kazuya
    Mimura, Shunsuke
    Mikami, Koichi
    TETRAHEDRON LETTERS, 2011, 52 (50) : 6682 - 6686
  • [29] 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
  • [30] Enantioselective Friedel-Crafts C2-alkylation of 3-substituted indoles with trifluoropyruvates and cyclic N-sulfonyl α-ketiminoesters
    Huang, Bing-Bing
    Wu, Liang
    Liu, Ren-Rong
    Xing, Ling-Ling
    Liang, Ren-Xiao
    Jia, Yi-Xia
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06): : 929 - 932