Electronic effects on π-facial stereoselectivity in electrophilic additions to allylic bonds: Stereoselective epoxidation of allylic fluorides

Article abstract of DOI:10.1016/0040-4039(91)80168-6

The electronic stabilization of the transition state in electrophilic additions to allylic bonds is discussed through m-CPBA oxidation of allylic fluorides; the stereoselectivity is interpreted by a transition-state model where the most electronegative atom (fluorine) is oriented at the inside position as supported by theoretical examinations.