A copper-catalyzed umpolung of N-2,2,2-trifluoroethylisatin ketimines for the enantioselective 1,3-dipolar cycloaddition with benzo[b]thiophene sulfones was developed. Using a catalyst system consisting of an (S,Sp)-tBu-Phosferrox ligand, Cu(OTf)2, and Cs2CO3, a range… Click to show full abstract
A copper-catalyzed umpolung of N-2,2,2-trifluoroethylisatin ketimines for the enantioselective 1,3-dipolar cycloaddition with benzo[b]thiophene sulfones was developed. Using a catalyst system consisting of an (S,Sp)-tBu-Phosferrox ligand, Cu(OTf)2, and Cs2CO3, a range of pentacyclic spirooxindoles containing pyrrolidine and benzo[b]sulfolane subunits were obtained in high efficiency with excellent regio-, diastereo-, and enantioselectivites under mild conditions. The practicality and versatility of the reaction were also demonstrated.
Journal Title: Organic letters
Year Published: 2022
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