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Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic 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.

SUBMITTER: Hayashi M

PROVIDER: S-EPMC5222469 | biostudies-literature | 2016 Oct

REPOSITORIES: biostudies-literature

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Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Hayashi Mikayo M Brown Lauren E LE Porco John A JA

European journal of organic chemistry 20161001 28

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 ...[more]

PMID: 28082832

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