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Regio- and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo-Pauson–Khand Cyclization

Authors

  • Prof. José Barluenga,

    Corresponding author
    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, Oviedo (Spain)
    • Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, Oviedo (Spain)
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  • Ana Álvarez-Fernández,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, Oviedo (Spain)
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  • Dr. Ángel L. Suárez-Sobrino,

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, Oviedo (Spain)
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  • Prof. Miguel Tomás

    1. Instituto Universitario de Química Organometálica “Enrique Moles”, Unidad Asociada al CSIC, Universidad de Oviedo, Julian Clavería 8, Oviedo (Spain)
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  • This research was partially supported by the Goverments of Spain (CTQ2010-20517-C02-01) and Principado de Asturias (IB08-088; Severo Ochoa-PCTI predoctoral fellowship to A.A.-F.)

Abstract

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Doing the two step: A very simple two-step access to polysubstituted cyclopentenones from terminal alkynes, [M(CO)6], and bromoalkenes is described. This protocol is an alternative to the intermolecular Pauson–Khand reaction, and can be used with a variety of bromoalkenes. Moreover, the final quenching allows the installation of reactive electrophiles (E). The enantiopure product cyclopentenones can be synthesized with an all-carbon-substituted quaternary stereocenter.

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