title: 1,4-Diketones from Cross-Conjugated Dienones: Potassium Permanganate-Interrupted Nazarov Reaction.
abstract: A domino potassium permanganate-interrupted Nazarov reaction to yield syn-2,3-disubstituted 1,4-diketones via a decarbonylative cleavage of the Nazarov oxyallyl intermediate, believed to be without precedent, is presented. This process allows syn substituents to be established stereospecifically on the 2-carbon bridge connecting the ketone carbonyl carbons, and the formation of one carbon-carbon and two carbon-oxygen bonds. Two carbon-carbon bonds are cleaved in this process.
authors.affiliation: Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada).
authors.forename: Yonghoon
authors.initials: Y
authors.lastname: Kwon
authors.affiliation: Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada).
authors.forename: Devon J
authors.initials: DJ
authors.lastname: Schatz
authors.affiliation: Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada). frederick.west@ualberta.ca.
authors.forename: Frederick G
authors.initials: FG
authors.lastname: West
keywords: 1,4-diketones; Nazarov reaction; electrocyclization; oxidative cleavage; potassium permanganate