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.
- difluorinated cyclooctenones
- stereoselective epoxidations
Fawcett, J., Griffith, G. A., Percy, J., & Uneyama, E. (2004). Unexpectedly selective formation and reactions of epoxycyclooctenones under microwave-mediated conditions. Organic Letters, 6(8), 1277-1280 . https://doi.org/10.1021/ol0496327