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DOI: 10.1055/s-0035-1561485
From Simple Cyclic 1,3-Ketoamides to Complex Spirolactams by Supported Heterogeneous Organocatalysis with PS-BEMP
Publikationsverlauf
Received: 12. Mai 2016
Accepted after revision: 08. Juni 2016
Publikationsdatum:
12. Juli 2016 (online)
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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 intermediateSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561485.
- Supporting Information
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