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Intramolecular Photoreactions of (5S)-5-Oxymethyl-2(5H)-furanones as a Tool for the Stereoselective Generation of Diverse Polycyclic Scaffolds

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    Intramolecular Photoreactions of (5S)-5-Oxymethyl-2(5H)-furanones as a Tool for the Stereoselective Generation of Diverse Polycyclic Scaffolds
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    † †Departament de Química and ‡Servei de RMN, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain
    *E-mail: [email protected]
    *E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2015, 80, 19, 9437–9445
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    https://doi.org/10.1021/acs.joc.5b01354
    Published September 9, 2015
    Copyright © 2015 American Chemical Society
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    Abstract

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    The photoactivated evolution of a series of enantiomerically pure 5-oxymethyl-2(5H)-furanones has been investigated. The observed intramolecular photoreactions have proven to be a straightforward entry to diverse and stereochemically rich fragment-molecules, most of which contain the privileged tetrahydropyran (THP) scaffold. The formation of the THP involves a 1,5-hydrogen atom transfer process, leading to a diradical intermediate that recombines to form a new σ C–C bond. These reactions take place under both sensitized and nonsensitized conditions, and they are highly stereoselective. When the substrate contains an allyl residue, the intramolecular [2 + 2] cycloaddition leading to cyclobutanes competes advantageously. When the substrate contains a THP residue, the cyclization involves the concomitant formation of [6,6]-spiroketals with nonanomeric relationships.

    Copyright © 2015 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b01354.

    • 1H and 13C NMR spectra of all new compounds and 2D NMR spectra for compounds 15, 17, 18, 19, 20, 21, 22, and 23 (PDF)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2015, 80, 19, 9437–9445
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.5b01354
    Published September 9, 2015
    Copyright © 2015 American Chemical Society
    Request reuse permissions

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