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Regioselective Isomerization of 2,3-Disubstituted Epoxides to Ketones: An Alternative to the Wacker Oxidation of Internal Alkenes

Jessica R. Lamb, Michael Mulzer, Anne M. LaPointe and Geoffrey W. Coates*

*Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States, Email: coatescornell.edu

J. R. Lamb, M. Mulzer, A. M. LaPointe, G. W. Coates, J. Am. Chem. Soc., 2015, 137, 15049-15054.

DOI: 10.1021/jacs.5b10419 (free Supporting Information)



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Abstract

An alternative pathway to the Wacker oxidation of internal olefins involving epoxidation of trans-alkenes followed by a mild and highly regioselective isomerization gives ketone isomers in good yield.

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Key Words

oxidation of alkenes, isomerizations


ID: J48-Y2015