Merging Organocatalysis and Gold Catalysis: Enantioselective Synthesis of Tetracyclic Indole Derivatives through a Sequential Double Friedel–Crafts Type Reaction

Authors

  • Charles C. J. Loh,

    1. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany), Fax: (+49) 241-809-2127
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  • Jan Badorrek,

    1. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany), Fax: (+49) 241-809-2127
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  • Prof. Dr. Gerhard Raabe,

    1. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany), Fax: (+49) 241-809-2127
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  • Prof. Dr. Dieter Enders

    Corresponding author
    1. Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany), Fax: (+49) 241-809-2127
    • Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany), Fax: (+49) 241-809-2127
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Abstract

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Yet another indole miracle: The sequential combination of organocatalysis and gold catalysis on C2,C3-unsubstituted indoles provides an efficient one-pot access to tetracyclic indole derivatives in very good yields and excellent enantioselectivities (see scheme). The double Friedel–Crafts type reaction, including a rare 7-endo-dig cyclisation, opens a new entry to highly enantioenriched anticancer drugs, such as DNA intercalators.

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