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

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 c...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2016-10, Vol.48 (19), p.3217-3231
Main Authors: Benmaati, Aouicha, Zahmani, Hadjira Habib, Hacini, Salih, Menéndez, José Carlos, Bugaut, Xavier, Rodriguez, Jean, Constantieux, Thierry
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1561485