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Gold(I)-Catalyzed Cascade Cycloadditions between Allenamides and Carbonyl-Tethered Alkenes: An Enantioselective Approach to Oxa-Bridged Medium-Sized Carbocycles

Authors

  • Hélio Faustino,

    1. Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, C/Jenaro de la Fuente, s/n, 15782 Santiago de Compostela (Spain)
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    • These authors contributed equally to this work.

  • Isaac Alonso,

    1. Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, C/Jenaro de la Fuente, s/n, 15782 Santiago de Compostela (Spain)
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    • These authors contributed equally to this work.

  • Prof. José L. Mascareñas,

    Corresponding author
    1. Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, C/Jenaro de la Fuente, s/n, 15782 Santiago de Compostela (Spain)
    • Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, C/Jenaro de la Fuente, s/n, 15782 Santiago de Compostela (Spain)

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  • Dr. Fernando López

    Corresponding author
    1. Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, C/Jenaro de la Fuente, s/n, 15782 Santiago de Compostela (Spain)
    2. Instituto de Química Orgánica General (CSIC), Juan de la Cierva, 3, 28006 Madrid (Spain)
    • Centro Singular de Investigación en Química Biológica y Materiales Moleculares (CIQUS) and Departamento de Química Orgánica, Universidad de Santiago de Compostela, C/Jenaro de la Fuente, s/n, 15782 Santiago de Compostela (Spain)

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  • This work was supported by the Spanish MINECO, (SAF2010-20822-C02-01/02, and Consolider-Ingenio 2010 CSD2007-00006), ERDF funds, and Xunta de Galicia (INCITE09209084PR, GRC2010/12). H.F. acknowledges the Fundação para a Ciência e Tecnologia (Portugal) and POPH/FSE for a PhD grant (SFRH/BD/60214/2009). Johnson-Matthey and Takasago are acknowledged for a gift of metals and segphos, respectively.

Abstract

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Gold standard: Allenamides react with aldehydes or ketones having γ, δ, or ε alkenyl groups, upon activation with suitable gold catalysts, to provide oxa-bridged systems containing seven- to nine-membered carbocycles, in a formal cascade cycloaddition. By using chiral phosphoramidite/gold or bisphosphine/gold catalysts it is possible to obtain the oxa-bridged seven- and eight-membered rings with good to high enantioselectivity.

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