Spiro compounds represent an important class of naturally occurring substances characterized by their highly pronounced biological properties [1]. The derivatives of Spirooxindole ring, spacially spiro [oxindole-isoxazolidine] find very wide biological application as antimicrobial, antitumour, anti HIV and antibiotic agents [2,3]. Due to the above reasons, In continuation of our ongoing research program on the synthesis of spiro heterocycles [4], herein we report for the firs time a regio and diastereoselective synthesis of a rare class of new spiro [indole-isoxazolidine] 3 in good yields from 1,3-dipolar cycloaddition of unactive isatin ketonitrone 1 and maleimides 2 under classical and solvent free conditions. Highly diastereo and regioselective cyclocondensation products were obtained under environmentally friendly ionic liquid conditions.