Synthesis 2016; 48(19): 3217-3231
DOI: 10.1055/s-0035-1561485
paper
© Georg Thieme Verlag Stuttgart · New York

From Simple Cyclic 1,3-Ketoamides to Complex Spirolactams by Supported Heterogeneous Organocatalysis with PS-BEMP

Aouicha Benmaati
a   Laboratoire de Chimie Fine, Faculté des Sciences Exactes et Appliquées, Université d’Oran-1, Ahmed Benbella BP-1524-Menouar, 31 000 Oran, Algeria
,
Hadjira Habib Zahmani
a   Laboratoire de Chimie Fine, Faculté des Sciences Exactes et Appliquées, Université d’Oran-1, Ahmed Benbella BP-1524-Menouar, 31 000 Oran, Algeria
,
Salih Hacini
a   Laboratoire de Chimie Fine, Faculté des Sciences Exactes et Appliquées, Université d’Oran-1, Ahmed Benbella BP-1524-Menouar, 31 000 Oran, Algeria
,
José Carlos Menéndez
b   Departamento de Química Orgánica y Farmacéutica Universidad Complutense, Facultad de Farmacia, Universidad Complutense, 28040 Madrid   Spain
,
Xavier Bugaut
c   Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille, France   Email: jean.rodriguez@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
,
Jean Rodriguez*
c   Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille, France   Email: jean.rodriguez@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
,
Thierry Constantieux*
c   Aix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille, France   Email: jean.rodriguez@univ-amu.fr   Email: thierry.constantieux@univ-amu.fr
› Author Affiliations
Further Information

Publication History

Received: 12 May 2016

Accepted after revision: 08 June 2016

Publication Date:
12 July 2016 (online)


In the memory of Professor Jean Normant

Abstract

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.

Supporting Information