Clarification of the Reactivity of 1,3,3,3-Tetrafluoropropene Oxides

Our computation has successfully clarified the reluctant behavior of trans- and cis-1,3,3,3-tetrafluoropropene oxides 1c toward nucleophiles and led to the expectation that these epoxides would react under the Bronsted acid activation conditions. Actually, this was the case, and these epoxides smoothly opened with CF3SO3H, whose elimination after the protection of the resultant OH group afforded the enol benzoates as the enolate precursors, which nicely allowed us to construct the corresponding aldol products by reactions with various aldehydes.