cyclization

broad substrate

triazoles

ring opening

cycloaddition reactions

amides

excellent enantioselectivities

amination

ACS Catalysis

A rhodium-catalyzed azide–alkyne cycloaddition of internal ynamides is described. The reaction could be performed in a wide range of solvents, including aqueous media, under mild conditions without careful exclusion of air and moisture, giving a variety of 5-amino-triazoles as a single regioisomer. The mechanism of regioselective cycloaddition was rationalized by means of density functional theory calculations.

Rhodium-Catalyzed Azide–Alkyne Cycloaddition of Internal Ynamides: Regioselective Assembly of 5-Amino-Triazoles under Mild Conditions