Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions.

Org Lett

Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RH, United Kingdom.

Published: April 2004

Topologically mobile difluorinated cyclooctenones undergo rapid, high-yielding, and completely stereoselective epoxidations with methyl(trifluoromethyl)dioxirane. The epoxides resist conventional hydrolysis but react smoothly in basic media under microwave irradiation to afford unique hemiacetals and hemiaminals in good yield. [reaction: see text]

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http://dx.doi.org/10.1021/ol0496327DOI Listing

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