Herein, we introduce a Ni-catalyzed asymmetric homobenzylic hydroamidation reaction that efficiently addresses the dual challenges of achieving regio- and enantioselectivity in the synthesis of β-(hetero)arylethylamides. By employing a transposed NiH catalysis approach, this method facilitates the formation of key chiral nickel-amido intermediates, enabling asymmetric insertion into alkenes to produce the desired β-arylamide products with excellent enantioselectivity. The reaction exhibits a high functional group tolerance and utilizes readily available starting materials of vinylarenes to react with dioxazolone as a robust amidating source. Notably, this approach was successfully applied to the synthesis of pharmaceutical compounds and natural products, such as Clobenzorex, Direx, Selegiline, Sacubitril, and Cipargamin.