A stereoselective tandem (4 + 3)-coupling of aziridines with 4-alkylidene indole malonates has been disclosed under Cu-catalysis involving a base-promoted annulation. The methodology serves as a potential approach toward the facile construction of fused azepinoindoles with good yields and diastereoselectivities. Late-stage natural product and drug modification as well as preliminary investigations for the enantioselective (4 + 3)-annulation are important practical features.