Stereoselective copper-catalyzed intramolecular alkene aminooxygenation: Effects of substrate and ligand structure on selectivity

A new protocol for diastereoselective copper-catalyzed intramolecular alkene aminooxygenation, which provides methyleneoxy-functionalized disubstituted pyrrolidines and five-membered cyclic ureas from the corresponding γ-alkenylsulfonamides and N-allylureas, is reported. In addition, some success was achieved in enantioselective desymmetrizations reactions. We discovered that the level of enantioselectivity and diastereoselectivity could be tuned by choice of copper(II) ligands and substrate N-substituent.