The introduction of a trifluoromethyl group into the 2′-position of spiro-pyrrolidine-3,3′-oxindoles is described. By using 1 mol% of a quinine-derived squaramide as catalyst, the 2,2,2-trfluoroethylamine (CF₃CH₂NH₂)-derived ketimine is transformed initially into a trifluoromethylimine through an umpolung reaction. The subsequent 1,3-dipolar cycloaddition gives the pharmaceutical important target compounds in excellent yields, enantioselectivities and diastereoselectivies.