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Publication - Professor Jonathan Clayden

    Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives


    Atkinson, RC, Fernández-Nieto, F, Rosellõ, JM & Clayden, J, 2015, ‘Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives’. Angewandte Chemie - International Edition, vol 54., pp. 8961-8965


    Available α-amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′-aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.

    Full details in the University publications repository