To shed light on the scope and limitations of palladium-catalyzed allylic alkylation in the presence of chiral trans-1,2-diaminocyclohexane-derived Fei-Phos as an effective phosphine ligand, the asymmetric palladium-catalysed alkylation of structurally diverse hard/soft nucleophiles, including allylic etherification of alcohols and the allylic alkylation of activated methylene compounds, indoles, and aromatic amines were investigated in this study; the corresponding products with various functional groups were achieved in good yield and with high enantioselectivity (up to 99% ee).