Weinreb β-Ketoamides in Enantioselective Organocatalysis: A Balance between Reactivity and Selectivity

Abstract

β-Dicarbonyl compounds have established themselves as substrates of choice in enantioselective organocatalysis because of their easy activation. Among them, β-diketones, β-diesters, and β-ketoesters lead the dance and there has been only limited work with other β-dicarbonyl compounds as pronucleophiles. In this Synpacts article, we wish to discuss our recent contributions to the introduction of Weinreb β-ketoamides in organocatalyzed transformations, where they can provide an interesting balance between reactivity and selectivity, with also interesting potentialities in terms of postfunctionalization.1 Introduction2 Preparation of Weinreb β-Ketoamides3 Michael Addition to Nitroolefins4 Multicomponent Synthesis of Tetrahydropyridines5 Outlook