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

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.

Automated summary

A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes has been demonstrated, providing access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity in a single step. The transformation proceeds through a novel acylation-terminated Heck-type sequence, with quantum chemical calculations indicating the involvement of C-H activation in the terminating acylation step.