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Publication - Professor Jonathan Clayden

    Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

    Citation

    Mas-Roselló, J, Okoh, M & Clayden, J, 2018, ‘Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles’. Chemical Communications, vol 54., pp. 10985-10988

    Abstract

    Lithiation of N′-arylureas derived from amino nitriles incorporating a (1R,2R)-2-aminocyclohexanol chiral auxiliary leads to diastereoselective migration of the aryl ring to the position α to the nitrile. The resulting N′-lithiated ureas undergo spontaneous cyclisation to iminohydantoins, which may be hydrolysed to give chiral 5,5-diarylhydantoins related to phenytoin, in enantioenriched form.

    Full details in the University publications repository