An unexpected cascade reaction of enyne-amides with sulfur-ylides has been developed. This cascade reaction involves cycloisomerization, dearomatic cyclopropanation, ringopening rearomatization, and subsequent cyclopropanation, differing from the common [2 + n] cyclization of enyne-amides. A variety of (spirocyclopropane)dihydrofuran derivatives have been efficiently and conveniently synthesized in a single vessel, exhibiting excellent diastereoselectivity and good functional group tolerance.