A highly efficient enantioselective synthesis of multisubstituted tetrahydrobenzofuran derivatives with four contiguous stereocenters was established by the dualcatalysis of a gold(I)/chiral N,N'-dioxide-cobalt(II) complex via a tandem cycloisomerization/Diels-Alder reaction of 2-alkynyl-2-alkenones and electron-deficient olefins. This strategy was not only featured with atom economy, remarkable efficiency