Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with Bpin: Experimental and Computational Studies.

The possibility to form new C-B bonds with aziridines using diboron derivatives continues to be a particularly challenging field in view of the direct preparation of functionalized β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report experimental and computational data that allows the individuation of the structural requisites and of reaction conditions necessary to open alkyl aziridines using bis(pinacolate)diboron (Bpin) in a regioselective nucleophilic addition reaction under copper catalysis.