Regio- and stereoselective epoxidation of chiral 1,4-cyclohexadienes

Abstract

The diastereoselectivities of epoxidations of diene amides 1b, 7, and 9 appear to depend on steric approach control with the involvement of amide conformers analogous to that observed by X-ray diffraction studies of epoxide 8 (Figure 1). This mechanistic framework should be useful for predicting the reactivity of diene amides related to 7 with other electrophilic reagents.