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

Published as part of the Special Section 9^th EuCheMS Organic Division Young Investigator Workshop

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 Introduction

2 Preparation of Weinreb β-Ketoamides

3 Michael Addition to Nitroolefins

4 Multicomponent Synthesis of Tetrahydropyridines

5 Outlook

Key words

β-dicarbonyl compounds - β-ketoamides - Michael additions - multicomponent reactions - organocatalysis - regioselectivity - stereoselectivity - Weinreb amides

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