Titanocene(III)-Mediated 5-exo-trig Radical Cyclization: En Route to Spirooxindole-Based Tetrahydrofuran and Bicyclic Lactone

摘要

The isatin core system is of immense importance due to the highly reactive prochiral C-3 position, which paves an easy way to construct large arrays of spirooxindole heterocyclic motifs. Herein, we depict an isatin-derived and 3,3'-disubstituted oxindole-appended, epoxy-acrylate undergoing Cp2Ti(III)Cl-mediated reductive oxirane-ring opening with concomitant intramolecular 5-exotrig radical cyclization leading to tetrahydrofuran-based oxaspirooxindole systems. The fused spirooxindole structural feature is embedded in many natural products and tends to exhibit a wide spectrum of biological activities. The presence of more than one quaternary center and the availability of multiple functional groups like hydroxyl, ester, or lactone in the resultant products expand the scope of synthetic applications of the newly acquired oxa-spirooxindole molecules.