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 β-aminoboronates, which are important compounds in drug discovery, being a bioisostere of β-aminoacids. We now report e...

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Autores principales: Favero, Lucilla, Menichetti, Andrea, Boldrini, Cosimo, Comparini, Lucrezia Margherita, Di Bussolo, Valeria, Di Pietro, Sebastiano, Pineschi, Mauro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8659106/
https://www.ncbi.nlm.nih.gov/pubmed/34885983
http://dx.doi.org/10.3390/molecules26237399
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author Favero, Lucilla
Menichetti, Andrea
Boldrini, Cosimo
Comparini, Lucrezia Margherita
Di Bussolo, Valeria
Di Pietro, Sebastiano
Pineschi, Mauro
author_facet Favero, Lucilla
Menichetti, Andrea
Boldrini, Cosimo
Comparini, Lucrezia Margherita
Di Bussolo, Valeria
Di Pietro, Sebastiano
Pineschi, Mauro
author_sort Favero, Lucilla
collection PubMed
description 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 (B(2)pin(2)) in a regioselective nucleophilic addition reaction under copper catalysis.
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spelling pubmed-86591062021-12-10 Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies Favero, Lucilla Menichetti, Andrea Boldrini, Cosimo Comparini, Lucrezia Margherita Di Bussolo, Valeria Di Pietro, Sebastiano Pineschi, Mauro Molecules Article 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 (B(2)pin(2)) in a regioselective nucleophilic addition reaction under copper catalysis. MDPI 2021-12-06 /pmc/articles/PMC8659106/ /pubmed/34885983 http://dx.doi.org/10.3390/molecules26237399 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Favero, Lucilla
Menichetti, Andrea
Boldrini, Cosimo
Comparini, Lucrezia Margherita
Di Bussolo, Valeria
Di Pietro, Sebastiano
Pineschi, Mauro
Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies
title Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies
title_full Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies
title_fullStr Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies
title_full_unstemmed Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies
title_short Copper-Catalyzed Ring-Opening Reactions of Alkyl Aziridines with B(2)pin(2): Experimental and Computational Studies
title_sort copper-catalyzed ring-opening reactions of alkyl aziridines with b(2)pin(2): experimental and computational studies
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8659106/
https://www.ncbi.nlm.nih.gov/pubmed/34885983
http://dx.doi.org/10.3390/molecules26237399
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