AbstractSpirocyclopentaneoxindole derivatives containing four consecutive stereocenters, including a spiro quaternary center, were constructed by an organocatalytic iminium–enamine cascade sequence in good yields (up to 86 %) with excellent enantiomeric (up to >99 % ee) and diastereomeric purities (up to >99:1 dr). This highly efficient procedure will allow diversity‐oriented syntheses of this intriguing class of compounds with potential biological activities.