Aouicha Benmaati1, Hadjira Habib Zahmani1, Salih Hacini1, J. Carlos Menéndez2, Xavier Bugaut3, Jean Rodriguez3, Thierry Constantieux3
1Laboratoire de Chimie Fine, Faculté des Sciences Exactes et Appliquées, Université d’Oran-1
2Departamento de Química Orgánica y Farmacéutica Universidad Complutense, Facultad de Farmacia, Universidad Complutense
3Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313
Tóm tắt
The reaction between cyclic 1,3-ketoamides and Michael acceptors in the presence of a catalytic amount of a polymer-supported organobase PS-BEMP has been developed for a direct access to spirocyclic 1,3-ketolactams through a domino Michael addition/hemiacetalization sequence. The products could be isolated in high chemical yields and purities after simple filtration, and the catalyst could be re-used without any re-activation. These spirolactams, containing a hemiaminal moiety, may be viewed as precursors of N-acyliminium intermediates upon Lewis acid activation, which allowed various subsequent functionalizations leading to original polycyclic lactams.
