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Publication - Professor Kevin Booker-Milburn

    Photochemically Produced Aminocyclobutanes as Masked Dienes in Thermal Electrocyclic Cascade Reactions

    Citation

    Elliott, LD & Booker-Milburn, KI, 2019, ‘Photochemically Produced Aminocyclobutanes as Masked Dienes in Thermal Electrocyclic Cascade Reactions’. Organic Letters, vol 21., pp. 1463-1466

    Abstract

    Cyclobutane products of a triplet sensitized enamide-alkene intramolecular [2+2] photocycloaddition have been shown to undergo fragmentation under acidic conditions. This lability has been exploited by inducing a complexity generating thermal electrocyclic cascade sequence involving the in situ formation of a cyclobutene, followed by electrocyclic ring opening, Diels-Alder cycloaddition and subsequent lactamization. This combination of excited state photochemistry and thermal elec-trocyclic cascade reactions allows simple planar molecules to be rapidly transformed into sp3 rich scaffolds.

    Full details in the University publications repository