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Synthesis of a new structural class of phenylalanine derivatives is described. Azidonation of Boc-L-Phe(4-I)-OMe via copper-ligand catalysis with sodium azide under microwave irradiation followed by regioselective copper-catalyzed azide-terminal alkyne cycloaddition provided new 4-(1,2,3-triazol-1-yl)-L-Phe derivatives. The developed protocol was also successfully employed to synthesize a late-stage modified Phe containing peptide.

Synthesis of 4-(1,2,3-triazol-1-yl)-L-phenylalanines