The palladium catalyzed [3+2] trimethylenemethane (TMM) cycloaddn. is an efficient method for the construction of cyclopentanes. Herein, a catalytic asym. protocol for the synthesis of spirocyclic oxindolic cyclopentanes, e.g., I, is reported. The title compds. were obtained in excellent yields and enantioselectivities. In this process, the chiral ligand controls the diastereo- as well as enantioselectivity, and the construction of up to three adjacent stereogenic centers.