Copper(I)-Catalyzed [3+1] Cycloaddition of Alkenyldiazoacetates and Iminoiodinanes: Easy Access to Substituted 2-Azetines

Authors

  • Prof. José Barluenga,

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985103450
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985103450
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  • Dr. Lorena Riesgo,

    1. Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain)
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  • Giacomo Lonzi,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985103450
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  • Prof. Miguel Tomás,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985103450
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  • Dr. Luis A. López

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985103450
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo (Spain), Fax: (+34) 985103450
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Abstract

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The copper(I)-catalyzed reaction of alkenyldiazoacetates and iminoiodinanes affords functionalized azetine derivatives. This process is consistent with the formation of an aziridinyldiazoacetate intermediate, which gives rise to the four-membered heterocycles by metal-catalyzed ring expansion. The resulting azetine structure is a direct precursor of azeditine-2-carboxylic acid derivatives (EWG=electron-withdrawing group).

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