Tetracyclic spiroindoline unit widely present as a core structure in many natural products, and has been the focus of extensive synthetic effort for a long time.[1-5] We have developeda facile and highly diastereoselective approach to the tetracyclic spiroindoline skeletonsbased on anintramolecular [3+2] annulation of indoles with 1,1-cyclopropane diesters.The reaction embraces a unique diastereochemical control by the diester groups and ligand which can switch the diastereoselection by the choice an appropriate ester group and ligand, thus allow the preparation of both cis and trans stereoisomers in high yields with excellent diastereocontrol.