Visible-light-mediated decarboxylative allylation of vinylcyclopropanes with α-keto acids toward β,γ-alkenyl ketones.

Abstract

β,γ-Alkenyl ketones are privileged structural motifs in organic synthesis with broad pharmaceutical relevance. In this context, we have successfully developed a visible-light-driven radical cross-coupling of α-keto acids with vinylcyclopropanes, enabling the direct synthesis of a variety of β,γ-alkenyl ketones without the need for external metal co-catalysts, oxidants, or additives. Mechanistic studies support a radical-polar crossover pathway involving photogenerated acyl radicals and ring-opening of VCPs. The synthetic utility of this method is demonstrated by the concise, five-step synthesis of the clinical drug Seratrodast.