Straightforward Synthesis of Bridged Azaoxa Skeletons: Gold-Catalyzed Aminoketalization of Garner’s Aldehyde-Derived Alkynes

Authors

  • Prof. Dr. Benito Alcaide,

    Corresponding author
    1. Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Facultad de Química, Unidad Asociada al CSIC, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 91-3944103
    • Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Facultad de Química, Unidad Asociada al CSIC, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 91-3944103
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  • Dr. Pedro Almendros,

    Corresponding author
    1. Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas, CSIC, Juan de la Cierva 3, 28006 Madrid (Spain), Fax: (+34) 91-5644853
    • Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas, CSIC, Juan de la Cierva 3, 28006 Madrid (Spain), Fax: (+34) 91-5644853
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  • Dipl.-Chem. Rocío Carrascosa

    1. Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Facultad de Química, Unidad Asociada al CSIC, Universidad Complutense de Madrid, 28040 Madrid (Spain), Fax: (+34) 91-3944103
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Abstract

original image

Building bridges with gold: Bridged azaoxa skeletons have been efficiently prepared from easily accessible alkynyloxazolidine substrates under mild reaction conditions (see scheme; Boc=tert-butoxycarbonyl). The reactions were found to proceed with complete control of the regio- and stereoselectivity of the products in the presence of a combined gold/silver and acid catalyst system.

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