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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 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.
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https://hal.archives-ouvertes.fr/hal-01415069
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Submitted on : Monday, December 12, 2016 - 5:53:31 PM
Last modification on : Tuesday, December 14, 2021 - 8:36:12 AM
Long-term archiving on: : Monday, March 27, 2017 - 9:17:24 PM

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Aouicha Benmaati, Hadjira Habib Zahmani, Salih Hacini, José Carlos Menéndez, Xavier Bugaut, et al.. From Simple Cyclic 1,3-Ketoamides to Complex Spirolactams by Supported Heterogeneous Organocatalysis with PS-BEMP. SYNTHESIS, Georg Thieme Verlag, 2016, 48 (19), pp.3217 - 3231. ⟨10.1055/s-0035-1561485⟩. ⟨hal-01415069⟩

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