Palladium(II)-Catalyzed Enantioselective Azidation of Unactivated Alkenes.

The first Pd-catalyzed enantioselective azidation of unactivated alkenes using readily accessible 1-azido-1,2-benziodoxol-3(1H)-one (ABX) as an azidating source has been established herein, which affords a wide variety of structurally diverse 3-N3-substituted piperidines in good yields with excellent enantioselectivities. The reaction features good functional group compatibility and mild reaction conditions. Notably, the employment of both an electrophilic azidating reagent and the sterically bulky chiral pyridinyl-oxazoline (Pyox) ligand is crucial to the successful reaction.