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Publication - Dr Natalie Fey

    Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids


    Abas, H, Mas-Roselló, J, Amer, MM, Durand, DJ, Groleau, RR, Fey, N & Clayden, J, 2019, ‘Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids’. Angewandte Chemie - International Edition, vol 58., pp. 2418-2422


    Both E- and Z-N′-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α-amino acids. Generation of their enolate derivatives in the presence of K
    and [18]crown-6 induces intramolecular migration of the alkenyl group from N′ to Cα with retention of double bond geometry. DFT calculations indicate a partially concerted substitution mechanism. Hydrolysis of the enantiopure products under acid conditions reveals quaternary α-alkenyl amino acids with stereodivergent control of both absolute configuration and double bond geometry.

    Full details in the University publications repository