NEW SYNTHETIC APPROACH TO FUNCTIONALIZED α METHYLENE γ BUTYROLACTAMS. A NEW ACCESS TO β HYDROXYMETHYLATED MODELS OF HIGH SYNTHETIC POTENTIALITY <br/> α MÉTHYLÈNE γ BUTYROLACTAMES Á HAUT POTENTIEL SYNTHÉTIQUE. SYNTHÈSE DES DÉRIVÉS γ ALKYLÉS β HYDROXYMÉTHYLÉS
GWENAËLLE LIBERGE(1, 2), STEPHANE LEBRUN(1, 2)ANDAXEL COUTURE(1, 3), PIERRE GRANDCLAUDON(1, 2*)
1. Université Lille Nord de France, F-59000 Lille, France
2. USTL, Laboratoire de Chimie Organique Physique, EA CMF 4478, Bâtiment C3(2), F-59655 Villeneuve d'Ascq, France
3. CNRS, UMR 8181 'UCCS', F-59655 Villeneuve d'Ascq, France
* Corresponding author: pierre.grandclaudon@univ-lille1.fr
Abstract
A new technique for the elaboration of α-methylene-γ-butyrolactams hydroxymethylated at the β-position has been developed. This new synthetic approach is based upon the preliminary assembly of N protected and γ-carboxylated analogues. A subsequent reduction / elimination sequence and ultimate N-deprotection completed the synthesis of the titled compounds.