Catalytic Stereoselective Synthesis of Diverse Oxindoles and Spirooxindoles from Isatins

A strategy for the efficient two-step synthesis of triazole derivatives of oxindoles and spirooxindoles is presented. Using a common set of <i>N</i>-propargylated isatins, a series of mechanistically distinct stereoselective reactions with different combinations of nucleophiles and catalysts provide access to diverse hydroxy-oxindoles, spiroindolones, and spirocyclic oxazoline structures. The resulting <i>N</i>-propargylated oxindoles are then converted to triazoles using copper-catalyzed azide–alkyne cycloaddition (CuAAC) reactions. Overall, this strategy affords a 64-member pilot-scale library of diverse oxindoles and spirooxindoles