Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): 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 beta-aminoboronates, which are important compounds in drug discovery, being a bioisostere of beta-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 (B(2)pin(2)) in a regioselective nucleophilic addition reaction under copper catalysis.