Synthesis of α-[2H]-amines via photodecarboxylation of N-phthaloyl α-amino acids

Abstract

N-phthaloyl activated α-amino acids can be efficiently decarboxylated with deuterium incorporation when irradiated in acetone / deuterium oxide mixtures or by irradiation of predeuterated N-phthaloyl α-amino acids (8 examples). Deprotection (hydrazinolysis) of these compounds leads to α-[2H]-amines with 95-99% deuterium content.