Fe(OTf)3 Catalyzed Annulation of 2,3-Disubstituted Indoles with Aziridines

被引:18
|
作者
Liu, Hua [1 ]
Zheng, Chao [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
关键词
annulation; indole; aziridine; Lewis acid; catalysis; ALLYLIC DEAROMATIZATION REACTION; FORMAL 3+2 CYCLOADDITION; CARBON BOND-CLEAVAGE; ENANTIOSELECTIVE SYNTHESIS; CASCADE DEAROMATIZATION; CYCLOPENTANNULATION; PYRROLOINDOLINES; CYCLIZATION; TRYPTOPHOLS; ALKALOIDS;
D O I
10.1002/cjoc.201400178
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Fe(OTf)(3) catalyzed [3+2] annulation reaction between 2,3-disubstituted indoles and N-Ts aziridines is described herein. A series of hexahydropyrrolo[3,4-b]indole derivatives bearing two consecutive quaternary carboncenters can be generated efficiently. The reaction features cheap catalyst, mild conditions and operational simplicity.
引用
收藏
页码:709 / 714
页数:6
相关论文
共 50 条
  • [1] Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes
    Larock, RC
    Yum, EK
    Refvik, MD
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22): : 7652 - 7662
  • [2] Palladium-catalyzed β-allylation of 2,3-disubstituted indoles
    Kagawa, Natsuko
    Malerich, Jeremiah P.
    Rawal, Viresh H.
    ORGANIC LETTERS, 2008, 10 (12) : 2381 - 2384
  • [3] Copper-catalyzed synthesis of 2,3-disubstituted Indoles
    Tanimori, Shinji
    Ura, Haruna
    Kirihatali, Mitsunori
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (24) : 3977 - 3980
  • [4] SYNTHESIS OF 2,3-DISUBSTITUTED INDOLES
    WIRTH, T
    BLECHERT, S
    SYNLETT, 1994, (09) : 717 - 718
  • [5] Synthesis of 3,3-Disubstituted Indolenines Utilizing the Lewis Acid Catalyzed Alkylation of 2,3-Disubstituted Indoles with Trichloroacetimidates
    Adhikari, Arijit A.
    Radal, Lea
    Chisholm, John D.
    SYNLETT, 2017, 28 (17) : 2335 - 2339
  • [6] Synthesis of 2,3-disubstituted indoles.
    Kennedy, AR
    Rainier, JD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 220 : U42 - U42
  • [7] NEW SYNTHESIS OF 2,3-DISUBSTITUTED INDOLES
    HILLARD, J
    REDDY, KV
    MAJUMDAR, KC
    THYAGARAJAN, BS
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (03) : 369 - 375
  • [8] Rhodium-Catalyzed Synthesis of 2,3-Disubstituted Indoles from α,β-Disubstituted Stryryl Azides
    Sun, Ke
    Liu, Sheng
    Bec, Patryk M.
    Driver, Tom G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (07) : 1702 - 1706
  • [9] Platinum-Catalyzed Allylation of 2,3-Disubstituted Indoles with Allylic Acetates
    Peng, Bai-Jing
    Wu, Wen-Ting
    Yang, Shyh-Chyun
    MOLECULES, 2017, 22 (12):
  • [10] Cu(OTf)2-Catalyzed Synthesis of 2,3-Disubstituted indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones
    Reddy, B. V. Subba
    Reddy, M. Ramana
    Rao, Y. Gopal
    Yadav, J. S.
    Sridhar, B.
    ORGANIC LETTERS, 2013, 15 (03) : 464 - 467