A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings
| Autor: | Thierry Constantieux, Damien Bonne, Sébastien Goudedranche, Jean Rodriguez, David Pierrot |
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| Přispěvatelé: | 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), ANR-11-BS07-0014,OEREKA,Réactions Enantiosélectives Organocatalysées à partir de Cétoamides(2011), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2014 |
| Předmět: |
Annulation
azepanes [CHIM.ORGA]Chemical Sciences/Organic chemistry Stereochemistry Chemistry domino reactions Metals and Alloys Enantioselective synthesis General Chemistry Optically active Catalysis Domino Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound Azepane Electrophile Materials Chemistry Ceramics and Composites enantioselective organocatalysis |
| Zdroj: | Chemical Communications Chemical Communications, Royal Society of Chemistry, 2014, 50, pp.15605-15608. ⟨10.1039/c4cc07731h⟩ Chemical Communications, 2014, 50, pp.15605-15608. ⟨10.1039/c4cc07731h⟩ |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c4cc07731h⟩ |
| Popis: | International audience; We report the first enantioselective organocatalyzed domino synthesis of azepane moieties. This temporary-bridge strategy is based on a conceptually original annulation of ambident electrophilic and 1,4-bis-nucleophilic a-ketoamides with 1,3-bis-electrophilic enals. The obtained oxygen-bridged azepanes can be selectively transformed into optically active azepanone, azepanol or azepanedione derivatives of high synthetic value. |
| Databáze: | OpenAIRE |
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