Asymmetric Double Oxidative [3 + 2] Cycloaddition for the Synthesis of CF3‑Containing Spiro[pyrrolidin-3,2′-oxindole]

An asymmetric double oxidative [3 + 2] cycloaddition is reported. Oxidation of 3-((2,2,2-trifluoroethyl)­amino)­indolin-2-ones and β-aryl-substituted aldehydes simultaneously and subsequent asymmetric cycloaddition in the presence of the chiral amino catalyst generated highly functionalized chiral CF3-containing spiro­[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C–C bonds from four C­(sp3)–H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.