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Publication - Professor John Bower

    Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes

    Citation

    Boyd, O, Wang, G-W, Sokolova, OO, Calow, ADJ, Bertrand, SM & Bower, JF, 2019, ‘Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes’. Angewandte Chemie - International Edition.

    Abstract

    Aminocyclopropanes equipped with pendant nucleophiles undergo C-C bond activation triggered carbonylative heterocyclization to provide 8-membered N-heterocycles. In these processes, intramolecular “capture” of a rhodacyclopentanone intermediate by an aryl or N-based nucleophile is followed by C-C or C-N bond forming “collapse” to the targets. These studies demonstrate how the combination of cyclopropane strain release and the templating effect of catalytically generated metallacycles can be harnessed to enable otherwise challenging medium ring closures.

    Full details in the University publications repository