Cu-catalyzed [1,3]-asymmetric methoxy rearrangement of N-methoxyanilines: mechanistic insight†

Abstract

Cu-catalyzed reactions of N-methoxy-2,6-dimethylanilines in the presence of a cationic Cu catalyst ligated to a chiral NHC ligand, which has an (ortho-carbamoyl)phenyl group on the nitrogen atom of (S,S)-diphenylimidazolidinylidene, furnished chiral ortho-quinol imines with good enantioselectivity. In addition, a cascade reaction involving the [1,3]-methoxy rearrangement followed by the Diels–Alder reaction yielded the corresponding three-dimensional molecules in a diastereo- and enantioselective manner.