Regio‐ and Stereoselective Synthesis of Spirooxindole–Pyrrolidine Hybrids Through 1,3‐Dipolar Cycloaddition: The Development of Potent α‐Glucosidase Inhibitors

A novel series of spirooxindole–pyrrolidine hybrids was synthesized and evaluated for their potential as α‐glucosidase inhibitors. These compounds were obtained via a regio‐ and stereoselective 1,3‐dipolar cycloaddition reaction between arylimines and an isatin‐derived alkene. Structural elucidation by NMR spectroscopy and single‐crystal X‐ray diffraction enabled unambiguous stereochemical assignment and provided insight into the diastereoselectivity of the reaction. Furthermore, the stereochemical outcome was found to be influenced by the electronic nature of the substituents on the arylimine moiety, offering valuable insight into the reaction mechanism. Among the synthesized compounds, bromine‐substituted analogues exhibited α ‐glucosidase inhibitory activity over 12‐fold greater than that of the reference drug acarbose, highlighting their potential as lead compounds for the development of next‐generation inhibitors.