Enantioselective Hydroamination/Cyclization Catalyzed by Organolanthanide Amides Derived from a New Chiral Ligand, (<i>S</i>)-2-(Pyrrol-2-ylmethyleneamino)-2′-(dimethylamino)-1,1′-binaphthyl

Abstract

A new series of bis-ligated organolanthanide amides, (1)2-LnN(SiMe3)2·C7H8 (Ln = Sm (2), Y (3), Yb (4)), have been prepared by the reaction of Ln[N(SiMe3)2]3 with the ligand (S)-2-(pyrrol-2-ylmethyleneamino)-2′-(dimethylamino)-1,1′-binaphthyl (1H) in good yields. They are active catalysts for the asymmetric hydroamination/cyclization reaction of aminoalkenes, affording cyclic amines in moderate to good conversions with moderate to good ee values.