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N-Fused Indolines through Non-Carbonyl-Stabilized Rhodium Carbenoid C[BOND]H Insertion of N-Aziridinyl Imines

Authors

  • Stuart J. Mahoney,

    1. Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1 (Canada), Fax: (+1) 519-746-0435
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  • Prof. Dr. Eric Fillion

    Corresponding author
    1. Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1 (Canada), Fax: (+1) 519-746-0435
    • Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1 (Canada), Fax: (+1) 519-746-0435
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Abstract

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Under rhodium catalysis, N-aziridinyl imines provided access to N-fused indolines through non-carbonyl-stabilized rhodium carbenoid C[BOND]H insertion. The utility of this methodology for the synthesis of architecturally complex heterocycles was further demonstrated by an expedient total synthesis of (±)-cryptaustoline (see scheme).

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