Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds
Petter Dunås1, Andrew J Paterson1, Gabriele Kociok-Köhn2
1Department of Chemistry and Chemical Engineering, Chalmers University of Technology, SE-41296 Gothenburg, Sweden. kann@chalmers.se.
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.
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