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

Guillaume Lejeune, Josep Font, Teodor Parella, Ramon Alibés, Marta Figueredo

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

Abstract

© 2015 American Chemical Society. 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.
Original languageEnglish
Pages (from-to)9437-9445
JournalJournal of Organic Chemistry
Volume80
Issue number19
DOIs
Publication statusPublished - 2 Oct 2015

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