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.

Enantiopure β-isocyano-boronic esters : synthesis and exploitation in isocyanide-based multicomponent reactions / M. Manenti, S. Gusmini, L. LO PRESTI, G. Molteni, A. Silvani. - In: MOLECULAR DIVERSITY. - ISSN 1381-1991. - (2022 Oct 19). [Epub ahead of print] [10.1007/s11030-022-10549-8]

Enantiopure β-isocyano-boronic esters : synthesis and exploitation in isocyanide-based multicomponent reactions

M. Manenti
Primo
;
L. LO PRESTI;G. Molteni
Penultimo
;
A. Silvani
Ultimo
2022

Abstract

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.
boronic acids; heterocycles; Isocyanides; multicomponent reactions; peptidomimetics
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/943873
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