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Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand–palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant‐ligand hydrogen bonding interaction. Dearomatized products were used in visible light‐mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan‐10‐ones, bicyclo[3.2.1]octan‐8‐ones and highly substituted cycloheptanones.
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Hayashi et al. (2016) studied this question.
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