Acylsilanes as a new type of "hard" carbon prenucleo-phile reacted with monosubstituted allyl reagents under Pd-catalyzed asymmetric allylic alkylation reaction conditions to provide products with high regio-, diastereo-, and enantioselectivities. The usefulness of the protocol has been demonstrated by the ready conversion of the allylated products into the corresponding alcohols, esters, and ketones with retention of stereochemistry as well as by the enantioselective synthesis of cis-3-ethyl-4-phenylpiperidine and cinnamomumolide.