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Lewis acid-catalyzed Friedel-Crafts reactions are useful for the synthesis of α-aryl-α- methylglycines. Reaction of methyl acetamidoacrylate 1 with anisole and phenol has been optimized and a short two-steps synthesis of amino acids α-methyl-α-(4-methoxyphenyl)glycine (5) and α-methyl-α-(4-hydroxyphenyl)glycine (9) was achieved with excellent yields. A new route is described to obtain both enantiomers of amino acids 5 and 9 by resolution of the racemic mixture using chiral high performance liquid chromatography.

Application of a new methodology for the synthesis of α-methyl-α-arylglycines using methyl acetamidoacrylate as an α-methylglycine cation equivalent