Bromination of N-phthaloylamino acid derivatives

Abstract

Hydrogen transfer to the bromine atom from the α-position of N-phthaloylamino acid derivatives is disfavoured to such an extent that bromination of N-phthaloyl derivatives of valine and phenylalanine occurs regiospecifically at the β-position, while halogenation of N-phthaloyl derivatives of glycylglycine and glycylglycylvaline occurs selectively at the C-terminal and non-terminal glycine residues, respectively.