Tagged: asymmetric synthesis
Lauren Brown and Mikayo Hayashi: Communication in the European Journal of Organic Chemistry
Congratulations to Lauren Brown, Mikayo Hayashi and Professor John Porco on their recent Communication in the European Journal of Organic Chemistry entitled “Asymmetric Dearomatization/ Cyclization Enables Access to Novel Chemotypes.”
Abstract: 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.