A Unified Strategy Toward 5-, 6-, and 7-Membered Nitrogen Heterocycles Through Free Radical then Metal-Mediated Functionalization of Ene-carbamates
| Autor: | Frédéric Robert, Redouane Beniazza, Jonathan Lusseau, Clément Poittevin, Yannick Landais, Stéphane Massip |
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| Přispěvatelé: | Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Institut Européen de Chimie et Biologie (IECB), Université de Bordeaux (UB)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Robert, Frédéric, Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Radical
chemistry.chemical_element 010402 general chemistry 01 natural sciences Metal Heck reaction Nucleophile Organic chemistry Ene reaction Grignard biology 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Heterocycle General Chemistry [CHIM.ORGA] Chemical Sciences/Organic chemistry biology.organism_classification Nitrogen 0104 chemical sciences chemistry Cyclization visual_art Aspidosperma visual_art.visual_art_medium Surface modification Vinylsulfones |
| Zdroj: | Advanced Synthesis and Catalysis Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2017, 359 (18), pp.3217-3225. ⟨10.1002/adsc.201700485⟩ Advanced Synthesis and Catalysis, 2017, 359 (18), pp.3217-3225. ⟨10.1002/adsc.201700485⟩ |
| ISSN: | 1615-4150 1615-4169 |
| DOI: | 10.1002/adsc.201700485⟩ |
| Popis: | International audience; Free-radical carbo-alkenylation of N-aryl, N-benzyl, and N-phenethyl-ene-carbamates with a disulfone provides vinylsulfones which may then be functionalized and engaged in Heck-type coupling to furnish highly substituted 5-, 6-and 7-membered nitrogen heterocycles. Grignardmediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the aspidosperma family. |
| Databáze: | OpenAIRE |
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