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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.

SUBMITTER: Favero L

PROVIDER: S-EPMC8659106 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Favero Lucilla L Menichetti Andrea A Boldrini Cosimo C Comparini Lucrezia Margherita LM Di Bussolo Valeria V Di Pietro Sebastiano S Pineschi Mauro M

Molecules (Basel, Switzerland) 20211206 23

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 (B2p ...[more]

PMID: 34885983

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