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Publication - Professor John Bower

    Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent

    An Aza-Prilezhaev Reaction


    Farndon, J, Young, T & Bower, J, 2018, ‘Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction’. Journal of the American Chemical Society, vol 140., pp. 17846-17850


    In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

    Full details in the University publications repository