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Catalytic, asymmetric synthesis of alpha,alpha-disubstituted amino acids



Catalytic, asymmetric synthesis of alpha,alpha-disubstituted amino acids



Tetrahedron Letters 44(10): 2045-2048, 3 March



Copper(salen) complex 1 has been found to catalyse the asymmetric alkylation of enolates derived from a variety of amino acids. There is a clear relationship between the size of the side chain in the substrate and the enantioselectivity of the process, so that the enantioselectivity decreases in the order alanine>aminobutyric acid>allylglycine>leucine>phenylalanine> valine. A transition state model which accounts for the influence of the size of the side chain on the enantioselectivity of the reactions is presented.

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