A regioselective acyloxylation with carboxylic acids at the proximal carbon of allenamides by an N-iodosuccinimide-mediated C-H functionalization is reported. The reaction proceeds rapidly, is scalable to a gram scale, and displays a broad substrate scope, providing an efficient and practical protocol for the synthesis of branched allylic esters. Notably, protected amino acids were tolerated under the reaction conditions and afforded allylic amino acid esters in moderate yields.