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

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.

SUBMITTER: Manenti M

PROVIDER: S-EPMC10520151 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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

Manenti Marco M Gusmini Simone S Lo Presti Leonardo L Molteni Giorgio G Silvani Alessandra A

Molecular diversity 20221019 5

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 m ...[more]

PMID: 36258147

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