Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

Abstract

A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity. The transformation proceeds through a novel acylation-terminated Heck-type sequence, and quantum chemical calculations indicate that C–H activation is involved in the terminating acylation step.