The stereospecific allylation of vinylstannanes with allylic halides proceeded in the presence of copper(I) iodide in DMSO-THF at room temperature. The stereospecificity of the reaction was dependent on the structures of vinylstannanes and allylic halides, and also the leaving group of allylic halides employed. Concerning the regioselectivity regarding allylic system, higher a-regioselection was observed in the reactions of allylic chlorides than in those of the corresponding iodides.