One‐Pot Enantioselective Aziridination of Olefins Catalyzed by a Copper( I ) Complex of a Novel Diimine Ligand by Using PhI(OAc) 2 and Sulfonamide as Nitrene Precursors

A novel chiral C 2 ‐symmetric 1,4‐diamine with multistereogenic centers at the backbone of the ligand has been synthesized from cheap natural product D ‐mannitol through multistep transformations. Its diimine derivative ( 3 a ) was found to be highly effective for the enantioselective control of the copper‐catalyzed asymmetric aziridination of olefin derivatives with PhINTs as the nitrene source, affording the corresponding N ‐sulfonylated azirindine derivatives in good to excellent yields with up to 99 % ee ( ee =enantiomeric excess). The catalyst system discovered in the present work was also extended to a one‐pot enantioselective aziridination by using sulfonamide/iodobenzene diacetate as the nitrene source. In this case, most reactions proceeded smoothly to give the corresponding products in moderate yields with good to excellent enantiomeric excesses (75–96 % ee ).