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

Lucilla Favero; Andrea Menichetti; Cosimo Boldrini; Lucrezia Margherita Comparini; Valeria Di Bussolo; Sebastiano Di Pietro; Mauro Pineschi

doi:10.3390/molecules26237399

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

Molecules. 2021 Dec 6;26(23):7399. doi: 10.3390/molecules26237399.

Authors

Lucilla Favero¹, Andrea Menichetti¹, Cosimo Boldrini¹, Lucrezia Margherita Comparini¹, Valeria Di Bussolo¹, Sebastiano Di Pietro¹, Mauro Pineschi¹

Affiliation

¹ Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, Italy.

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: DFT study; aminoboronates; aziridines; copper catalysis; diboron reagents.