Various isocyanide-based multicomponent reactions prove to be highly reliable when beta-substituted beta-amino boronic esters are employed as the amine component, allowing the efficient synthesis of unprecedented peptidomimetics and heteroatom-rich boron-containing small molecules. In particular, the scope of the Ugi reaction is widely exploited, to give a family of enantiopure beta-substituted beta-amido boronates. The Ugi-azide and the van Leusen reactions allow to joint together prominent pharmacophoric moieties, such as beta-amino boronic acids on one side, and tetrazole or imidazole rings on the other side, realizing a successful application of the molecular hybridization concept.

Exploiting Enantiopure beta-Amino Boronic Acids in Isocyanide-Based Multicomponent Reactions / M. Manenti, S. Gusmini, L. Lo Presti, A. Silvani. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 25(2022), pp. e202200435.1-e202200435.7. [10.1002/ejoc.202200435]

Exploiting Enantiopure beta-Amino Boronic Acids in Isocyanide-Based Multicomponent Reactions

M. Manenti
Primo
;
L. Lo Presti
Penultimo
;
A. Silvani
2022

Abstract

Various isocyanide-based multicomponent reactions prove to be highly reliable when beta-substituted beta-amino boronic esters are employed as the amine component, allowing the efficient synthesis of unprecedented peptidomimetics and heteroatom-rich boron-containing small molecules. In particular, the scope of the Ugi reaction is widely exploited, to give a family of enantiopure beta-substituted beta-amido boronates. The Ugi-azide and the van Leusen reactions allow to joint together prominent pharmacophoric moieties, such as beta-amino boronic acids on one side, and tetrazole or imidazole rings on the other side, realizing a successful application of the molecular hybridization concept.
Boronic acids; Cyclic boronates; Heterocycles; 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/2434/933650
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