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

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.

Automated summary

Utilizing isocyanide-based multicomponent reactions, unprecedented boron-containing small molecule peptidomimetics were efficiently synthesized, successfully applying the concept of molecular hybridization.