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  • Title: Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives.
    Author: Atkinson RC, Fernández-Nieto F, Mas Roselló J, Clayden J.
    Journal: Angew Chem Int Ed Engl; 2015 Jul 27; 54(31):8961-5. PubMed ID: 26083236.
    Abstract:
    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.
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