A highly enantioselective palladium-catalyzed intramolecular Heck reaction of unactivated alkenes is developed, which provides a powerful route to access a broad range of chiral 3,3-disubstituted-2,3-dihydrobenzofurans bearing all-carbon quaternary stereocenter of interest in pharmaceutical research. Its salient features include high yield, excellent chemo- and enantioselectivity, mild condi-tions, a broad substrate scope as well as versatile transformations of the product.