Highly enantioselective synthesis of dihydroquinazolinones through Sc(OTf)3-catalyzed intramolecular amidation of imines

•The fluorous bis(oxazolines) was found to be a general, highly enantioselective ligand for the intramolecular amidation of imines.•A series of chiral dihydroquinazolinones were obtained in 76–94% yields with enantioselectivities up to 98%.•The fluorous ligand can be easily recovered and reused at least three times without significant loss of enantioselectivity.

A Sc(OTf)3-catalyzed intramolecular amidation of imines with a novel fluorous bis(oxazolines) as ligand is presented. The corresponding chiral dihydroquinazolinones were obtained in 76–94% yield with enantioselectivities up to 98%. The fluorous ligand can be easily recovered and reused at least three times without significant loss of enantioselectivity.

Graphical abstractA Sc(OTf)3-catalyzed intramolecular amidation of imines with a novel fluorous bis(oxazolines) as ligand is presented. The corresponding chiral dihydroquinazolinones were obtained in 76–94% yield with enantioselectivities up to 98%. The fluorous ligand can be easily recovered and reused at least 3 times without significant loss of enantioselectivity.Figure optionsDownload full-size imageDownload as PowerPoint slide