Hayashi, MikayoBrown, Lauren E.Porco, John A.2018-01-302018-01-302016-10Mikayo Hayashi, Lauren E Brown, John A Porco. 2016. "Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.." European J Org Chem, Volume 2016, Issue 28, pp. 4800 - 4804.1434-193Xhttps://hdl.handle.net/2144/26486Enantioenriched, 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.4800 - 4804Science & technologyPhysical sciencesChemistry, organicChemistryAsymmetric catalysisDearomatizationPhotocatalysisRadical reactionsPolycyclesMedicinal and biomolecular chemistryOrganic chemistryArticle10.1002/ejoc.201601003