From Simple Cyclic 1,3-Ketoamides to Complex Spirolactams by Supported Heterogeneous Organocatalysis with PS-BEMP
| Autor: | José Carlos Menéndez, Jean Rodriguez, Aouicha Benmaati, Thierry Constantieux, Xavier Bugaut, Salih Hacini, Hadjira Habib Zahmani |
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| Přispěvatelé: | Universidad Complutense de Madrid = Complutense University of Madrid [Madrid] (UCM), Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Fine, Faculté des Sciences Exactes et Appliquées, Université d’Oran-1, Ahmed Benbella BP-1524-Menouar, 31 000 Oran, Algeria, Departamento de Química Orgánica y Farmacéutica Universidad Complutense, Facultad de Farmacia, Universidad, Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
spirolactam
010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Catalysis Domino 0104 chemical sciences chemistry.chemical_compound supported organobase chemistry Organocatalysis Michael addition Hemiaminal Michael reaction Moiety Organic chemistry N-acyliminium intermediate heterogeneous organocatalysis Lewis acids and bases |
| Zdroj: | SYNTHESIS SYNTHESIS, Georg Thieme Verlag, 2016, 48 (19), pp.3217-3231. ⟨10.1055/s-0035-1561485⟩ Synthesis: Journal of Synthetic Organic Chemistry Synthesis: Journal of Synthetic Organic Chemistry, 2016, 48 (19), pp.3217-3231. ⟨10.1055/s-0035-1561485⟩ |
| ISSN: | 0039-7881 1437-210X |
| DOI: | 10.1055/s-0035-1561485⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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