A new approach to the synthesis of N-alkylated 2-substituted azetidin-3-ones.
Fiche publication
Date publication
mai 2006
Auteurs
Membres identifiés du Cancéropôle Est :
Pr SAPI Janos, Dr GERARD Stéphane
Tous les auteurs :
Gerard S, Raoul M, Sapi J
Lien Pubmed
Résumé
We report a one-pot methodology for the synthesis of N-alkylated 2-substituted azetidin-3-ones based on a tandem nucleophilic substitution followed by intramolecular Michael reaction of primary amines with alkyl 5-bromo-4-oxopent-2enoates, obtained in turn in three steps from levulinic acid. A mechanistic interpretation of these reactions and an attempted enantioselective approach are also described. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Référence
Eur J Org Chem. 2006 May 12;10:2440-5.