A small library of highly tunable chiral Clickphine P, N-ligands has been prepared in an enantioselective fashion by CuI-catalyzed asymmetric propargylic amination using a single chiral complex and a subsequent in situ cycloaddition click reaction. The scope of the propargylic amination to yield optically active triazolyl amines is described. The amines are transformed in a one-pot procedure to the corresponding Ir–Clickphine complexes, which ...