Palladium-catalyzed asymmetric formal [3 + 2] cycloaddition of vinyl cyclopropanes and aldimines or isatin-derived ketimines proceeded smoothly in the presence of chiral phosphoramidite ligands. The corresponding highly functionalized and optically enriched pyrrolidine or spiro[pyrrolidin-3,2'-oxindole] derivatives are obtained in up to 94% yield and with up to 96% ee and 7:1 dr.