1,3-dipolar cycloaddition of (E)-arylidene-(2H)-indanones 1 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-NO2C6H4) and (E)-2-arylidene-(2H)-tetralones 2 (Ar = Ph, p-MeC6H4, p-MeOC6H4, p-ClC6H4, p-NO2C6H4) to N-metalated azomethine ylides 3 generated from methyl N-arylideneglycinate in the presence of silver acetate produces in good yields novel methyl 1-oxo-2',4'-diaryl-1,3-dihydrospiro[indene-2,3’-pyrrolidine]-5'-carboxylates 4 and methyl 1-oxo-2',4'-diaryl-3,4-dihydro-1H-spiro[naphthalene-2,3'-pyrrolidine]-5'- carboxylates 5. The cycloaddition proceeds in regio- and stereoselective manner (100%) at room temperature to afford respectively the syn-endo cycloadducts 4 and 5 via metallo-azomethine ylides. The regio- and stereochemistry of the spiranic adducts have been established on the basis of spectroscopic data and elemental analysis, corroborated by single-crystal X-ray crystallographic analysis of the heterocycles 4ci, 4bg and 5bi. The endo-pyrrolidines 4 were brominated by N-bromosuccinimide to give finally the dehydrobrominated 3, 4-dihydro-2H-pyrrole derivatives 6. The spiro-adducts 4 and their corresponding oxidation products 6 are fluorescent in solution.