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, Geoffrey W. Coates

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

We report an alternative pathway to the Wacker oxidation of internal olefins involving epoxidation of trans-alkenes followed by a mild and highly regioselective isomerization to give the major ketone isomers in 66-98% yield. Preliminary kinetics and isotope labeling studies suggest epoxide ring opening as the turnover limiting step in our proposed mechanism. A similar catalytic system was applied to the kinetic resolution of select trans-epoxides to give synthetically useful selectivity factors of 17-23 for benzyl-substituted substrates.

Original languageEnglish (US)
Pages (from-to)15049-15054
Number of pages6
JournalJournal of the American Chemical Society
Volume137
Issue number47
DOIs
StatePublished - Dec 2 2015
Externally publishedYes

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