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Oxidative Ring Contraction of Cyclobutenes: General Approach to Cyclopropylketones including Mechanistic Insights

Andreas N. Baumann, Franziska Schüppel, Michael Eisold, Andrea Kreppel, Regina de Vivie-Riedle* and Dorian Didier*

*Department of Chemistry and Pharmacy, Ludwig-Maximilians-University, Butenandtstraße 5-13, 81377 Munich, Germany, Email: dorian.didiercup.uni-muenchen.de, regina.de_viviecup.uni-muenchen.de

A. N. Baumann, F. Schüppel, M. Eisold, A. Kreppel, R. de Vivie-Riedle, D. Didier, J. Org. Chem., 2018, 83, 4905-4921.

DOI: 10.1021/acs.joc.8b00297 (free Supporting Information)


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Abstract

An oxidative ring contraction of easily accessible cyclobutene derivatives enables a selective formation of cyclopropylketones in the presence of mCPBA as oxidant. This functional group tolerant transformation proceeds under mild conditions at room temperature.


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Key Words

cyclopropanes, mCPBA


ID: J42-Y2018