1,4-Diketones from Cross-Conjugated Dienones: Potassium Permanganate-Interrupted Nazarov Reaction

Yonghoon Kwon; Devon J Schatz; Frederick G West

doi:10.1002/anie.201503696

1,4-Diketones from Cross-Conjugated Dienones: Potassium Permanganate-Interrupted Nazarov Reaction

Angew Chem Int Ed Engl. 2015 Aug 17;54(34):9940-3. doi: 10.1002/anie.201503696. Epub 2015 Jul 3.

Authors

Yonghoon Kwon¹, Devon J Schatz¹, Frederick G West²

Affiliations

¹ Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada).
² Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, Alberta, T6G 2G2 (Canada). frederick.west@ualberta.ca.

PMID: 26138361
DOI: 10.1002/anie.201503696

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.

Keywords: 1,4-diketones; Nazarov reaction; electrocyclization; oxidative cleavage; potassium permanganate.