A highly enantioselective one-pot synthesis of cyclopropane-fused tetrahydroquinolines bearing carbonyl functionalities, which are difficult to synthesize using conventional methods, is reported. Employing readily accessible alkene-tethered anthranilaldehydes, hydrazone formation and subsequent Ru-catalyzed intramolecular cyclopropanation furnish the desired products in ≤87% yield and ≤95% ee under mild conditions. Various anthranilaldehydes, functionalized alkenes, and N-aryl sulfonyl groups are tolerated, and a series of synthetic transformations were conducted to demonstrate the practical utility.