The olefin isomerization/enantioselective intramolecular Alder-ene reaction cascade was achieved by using a cationic rhodium (I)/(R)-BINAP complex as a catalyst. A variety of substituted dihydrobenzofurans and dihydronaphthofurans were obtained from phenol-or naphthol-linked 1, 7-enynes, respectively, with good yields and ee values.