Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B₂pin₂: Experimental and Computational Studies

Abstract

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 (B2pin2) in a regioselective nucleophilic addition reaction under copper catalysis.

Keywords

• copper catalysis
• diboron reagents
• aziridines
• aminoboronates
• DFT study