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

Abstract

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 CF 3 -containing spiro[pyrrolidin-3,2′-oxindole] with four contiguous stereocenters stereoselectively, which is characterized by directly constructing two C−C bonds from four C(sp 3 )−H bonds. This new method features mild conditions, broad substrate scope, and excellent functional group compatibility.