Alkene Oxyamination: One-Pot Synthesis of Unprotected N–H Amino γ-Lactones

We report a mild, Rh-catalyzed alkene oxyamination protocol for the synthesis of N-H unprotected amino γ-lactones. This method enables efficient coupling of a broad range of alkenyl carboxylic acids (16 examples) with structurally complex, <i>O</i>-activated hydroxylamines (9 examples). The utility of the transformation is further demonstrated through the late-stage functionalization of active pharmaceutical ingredients (3 examples). This operationally simple, one-pot process proceeds via sequential intermolecular, stereospecific olefin aziridination followed by intramolecular aziridine ring-opening.