Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline

A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot L-proline promoted three-component reaction between substituted benzaldehydes, anilines and enolizable aldehydes, followed by the in situ reduction of the resulting b-aminoaldehydes to the corresponding c-aminoalcohols and final intramolecular cyclization of the latter by way of the intermediate tosylates, formed in situ.Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Amongero, Marcela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentin