Asymmetric dearomatization/cyclization enables access to polycyclic chemotypes
Brown, Lauren E.
Porco, John A.
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CitationMikayo 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.
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.