Reported here is an efficient enantioselective hydrogenation of cyclic oxocarbenium ions generated in situ through collapse of corresponding acetal substrates. The asymmetric approach provides a straightforward access to a variety of chiral α-aryl substituted 1,3-dihydroisobenzofurans in high yields with excellent enantioselectivities.α-Alkynyl substituted 1,3-dihydroisobenzofurans were also proved to be suitable substrates. In addition, when the reaction was performed at gram scale, the desired product was obtained in good yields with excellent enantioselectivity.