Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes | Zendy

Hayashi Mikayo | Zendy; Brown Lauren E. | Zendy; Porco John A. | Zendy

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Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes

Author(s) -

Hayashi Mikayo,

Brown Lauren E.,

Porco John A.

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201601003

Subject(s) - chemistry , ligand (biochemistry) , chemotype , enantioselective synthesis , palladium , bicyclic molecule , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , receptor , biochemistry , chromatography , essential oil

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[4.3.1.0 1,4 ]decan‐10‐ones, bicyclo[3.2.1]octan‐8‐ones and highly substituted cycloheptanones.

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