Enantiopure β-isocyano-boronic esters: synthesis and exploitation in isocyanide-based multicomponent reactions.
Boronic acids
Heterocycles
Isocyanides
Multicomponent reactions
Peptidomimetics
Journal
Molecular diversity
ISSN: 1573-501X
Titre abrégé: Mol Divers
Pays: Netherlands
ID NLM: 9516534
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
received:
29
07
2022
accepted:
07
10
2022
medline:
4
10
2023
pubmed:
19
10
2022
entrez:
18
10
2022
Statut:
ppublish
Résumé
Various boron-containing isocyanides have been efficiently synthesized from the corresponding enantiopure β-substituted β-amino boronic acid pinacol esters, without need for protecting group interconversion, through a two-step, purification-free procedure. They were employed in a variety of isocyanide-based multicomponent reactions, proving to be reliable components for all of them and allowing the efficient synthesis of unprecedented, boron-containing peptidomimetics and heteroatom-rich small molecules, including biologically relevant cyclic boronates. Jointing together the β-amido boronic acid moiety, deriving from the isocyanide component, with prominent pharmacophoric rings emerging from the multicomponent process, a successful application of the molecular hybridization concept could be realized.
Identifiants
pubmed: 36258147
doi: 10.1007/s11030-022-10549-8
pii: 10.1007/s11030-022-10549-8
pmc: PMC10520151
doi:
Substances chimiques
Cyanides
0
Boron
N9E3X5056Q
Esters
0
Boronic Acids
0
Peptidomimetics
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2161-2168Informations de copyright
© 2022. The Author(s).
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