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1,4‐Diketones from Cross‐Conjugated Dienones: Potassium Permanganate‐Interrupted Nazarov Reaction
Author(s) -
Kwon Yonghoon,
Schatz Devon J.,
West Frederick G.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503696
Subject(s) - chemistry , potassium permanganate , conjugated system , yield (engineering) , ketone , carbon fibers , medicinal chemistry , organic chemistry , materials science , composite number , metallurgy , composite material , polymer
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.