The switchable skeletal rearrangement for the construction of amino indanones and tetrahydroisoquinolones frameworks had been developed. In the presence of a chiral phosphoric acid catalyst, the reaction gave the amino indanones in high yields and good to excellent ee (85-98%), while the methoxyl substituent at the 5-position of dihydroisobenzofuran acetal selectively gave isoquinolinones products in good to excellent ee (46-98%). Furthermore, DFT calculations were performed to explain the regioselectivity of the switchable transformation pathways.