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Chemoselective C[BOND]C Bond Cleavage of Epoxide Motifs: Gold(I)-Catalyzed Diastereoselective [4+3] Cycloadditions of 1-(1-Alkynyl)oxiranyl Ketones and Nitrones

Authors

  • Tao Wang,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-5039
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  • Prof. Dr. Junliang Zhang

    Corresponding author
    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-5039
    2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, (P.R. China)
    • Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China), Fax: (+86) 21-6223-5039
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Abstract

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Cutting carbon! A novel facile strategy for the C[BOND]C bond cleavage of oxiranyl ketones has been developed. Carbophilic gold(I) activation of the alkyne side chain mediates a heterocyclization and subsequent C[BOND]C bond cleavage (see scheme).

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