Two spiro[indoline-3,3′-pyrrolizine] derivatives have been synthesized in good yield with high regio- and stereospecificity using one-pot reactions between readily available starting materials, namely L-proline, substituted 1 H -indole-2,3-diones and electron-deficient alkenes. The products have been fully characterized by elemental analysis, IR and NMR spectroscopy, mass spectrometry and crystal structure analysis. In (1′ RS ,2′ RS ,3 SR ,7a′ SR )-2′-benzoyl-1-hexyl-2-oxo-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,3′-pyrrolizine]-1′-carboxylic acid, C 28 H 32 N 2 O 4 , (I), the unsubstituted pyrrole ring and the reduced spiro-fused pyrrole ring adopt half-chair and envelope conformations, respectively, while in (1′ RS ,2′ RS ,3 SR ,7a′ SR )-1′,2′-bis(4-chlorobenzoyl)-5,7-dichloro-2-oxo-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,3′-pyrrolizine], which crystallizes as a partial dichloromethane solvate, C 28 H 20 Cl 4 N 2 O 3 ·0.981CH 2 Cl 2 , (II), where the solvent component is disordered over three sets of atomic sites, these two rings adopt envelope and half-chair conformations, respectively. Molecules of (I) are linked by an O—H...·O hydrogen bond to form cyclic R 6 6 (48) hexamers of \overline{3} ( S 6 ) symmetry, which are further linked by two C—H...O hydrogen bonds to form a three-dimensional framework structure. In compound (II), inversion-related pairs of N—H...O hydrogen bonds link the spiro[indoline-3,3′-pyrrolizine] molecules into simple R 2 2 (8) dimers.