Synthesis of a serie of novel spiropyrrolidines has been accomplished by regio and stereoselective 1,3-dipolar cycloaddition of N-metalated azomethine ylides, generated in situ from α-iminoesters 1 in the presence of silver acetate and triethylamine, to 3-arylidene-1-phenyl-pyrrolidine-2,5-diones 2. The structure of the spiroadducts 3 was elucidated by 1H and 13C NMR study. The proposed regio and stereochemistry of spiranic compound has been corroborated by single crystal X-ray crystallographic analyses of compound spiro[3-(4-chlorophényl)-5-(méthylphényl)-2-carbomethoxypyrrolidine-4-(N-phénylsuccinimide)]3bh.
S. Haddad, I. Jalloul, S. Boudriga, M. Askri, M. Knorr, Y. Rousselin, M. M. Kubicki
Spiropyrrolidine, 1,3-dipolar cycloaddition, N-metalated azomethine ylides, crystal structure