The development of efficient and straightforward methods for obtaining all optically active isomers of structurally rigid spirocycles from readily available starting materials is of great value in drug discovery and chiral ligand development. However,t he stereodivergent synthesis of spirocycles bearing multiple stereocenters remains an unsolved challenge owing to steric hindrance and ring strain. Herein, we report an enantioand diastereodivergent synthesis of rigid spirocycles through dual-metal-catalyzed [3+ +2] annulation of oxy p-allyl metallic dipoles with less commonly employed nucleophilic dipoles (imino esters). Aseries of spiro compounds bearing apyrroline and an olefin were easily synthesized in an enantio-and diastereodivergent manner (up to 19:1 dr, > 99 %e e), which showed great promise as an ew type of N-olefin ligand. Preliminary mechanistic studies were also carried out to understand the process of this bimetallic catalysis.