Enantioselective ortho-C–H Addition of Aromatic Amines to Alkenes by Bulky Chiral Anilido-Oxazoline Scandium Complexes

The enantioselective C-H addition of anilines to alkenes represents an ideal protocol for the synthesis of chiral aromatic amines in terms of step- and atom-economy. However, this field remains predominantly unexplored. Herein, a series of newly designed bulky chiral anilido-oxazoline ligand precursors were synthesized, and the corresponding rare-earth metal alkyl complexes were obtained successfully. The resultant scandium complexes exhibit high regioselectivity for the ortho-C-H addition of tertiary anilines to unactivated alkenes, providing a wide range of chiral alkylated anilines in high yields (up to 98% yield) with excellent enantioselectivity (up to 98% ee). Moreover, the addition products can be easily converted into biorelevant derivatives and pharmacophore-containing skeletons.