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

Aouicha Benmaati; Hadjira Habib Zahmani; Salih Hacini; José Carlos Menéndez; Xavier Bugaut; Jean Rodriguez; Thierry Constantieux

doi:10.1055/s-0035-1561485

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(19): 3217-3231
DOI: 10.1055/s-0035-1561485

paper

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

Aouicha Benmaati

^aLaboratoire 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

^aLaboratoire de Chimie Fine, Faculté des Sciences Exactes et Appliquées, Université d’Oran-1, Ahmed Benbella BP-1524-Menouar, 31 000 Oran, Algeria

,

Salih Hacini

^aLaboratoire 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

^bDepartamento de Química Orgánica y Farmacéutica Universidad Complutense, Facultad de Farmacia, Universidad Complutense, 28040 Madrid Spain

,

Xavier Bugaut

^cAix-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*

^cAix-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*

^cAix-Marseille Université, Centrale Marseille, CNRS iSm2 UMR 7313, 13397, Marseille, France eMail: jean.rodriguez@univ-amu.fr eMail: thierry.constantieux@univ-amu.fr

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Abstract

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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.

Key words

supported organobase - Michael addition - spirolactam - heterogeneous organocatalysis - N-acyliminium intermediate

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Referenzen

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31 CCDC 1429887 (3ed), CCDC 1429886 (5ld), and CCDC 1430278 (8fb) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

Zusatzmaterial

Supporting Information