Aza-Heck cyclization of alkene-tethered oxime esters has received considerable attention as an effective strategy for synthesizing 1-pyrroline derivatives. However, the achievement of tandem aza-Heck reaction with alkyl electrophiles remains a challenge. Herein, we report a palladium-catalyzed tandem aza-Heck reaction of alkene-tethered oxime esters with cyclopropanols. This catalytic system features mild conditions and broad substrate scopes, allowing the direct synthesis of structurally diverse 1-pyrroline derivatives in good yields.