Tiffeneau–Demjanov Rearrangement by Using alpha-Chloro-diazo-acetate: A Direct Access to alpha-Chlorinated Medium-Size-Ring Ketones via Ring Enlargement
| Autor: | Jean-Luc Parrain, Sylvana Cohen, Maxime Dousset, Gaëlle Chouraqui, Karel Le Jeune |
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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), 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: |
010405 organic chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry alpha-halogenation Organic Chemistry Intermolecular force tetrasubstituted stereocenter 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry ring expansion chloro(diazo)acetate cyclic ketones Yield (chemistry) Organic chemistry Diazo Lewis acids and bases Tiffeneau–Demjanov rearrangement |
| Zdroj: | SYNTHESIS SYNTHESIS, Georg Thieme Verlag, 2016, 48, pp.2396-2401. ⟨10.1055/s-0035-1561413⟩ Synthesis: Journal of Synthetic Organic Chemistry Synthesis: Journal of Synthetic Organic Chemistry, 2016, 48, pp.2396-2401. ⟨10.1055/s-0035-1561413⟩ |
| ISSN: | 0039-7881 1437-210X |
| Popis: | International audience; alpha-Chloro(diazo)acetate can be readily used in an intermolecular ring expansion catalyzed by a boron Lewis acid to construct alpha-chlorinated medium-size cyclic ketones. This intermolecular Tiffeneau–Demjanov reaction proceeds in good yield from easily prepared or commercially available starting materials and allows the concomitant formation of a tetrasubstituted stereocenter. |
| Databáze: | OpenAIRE |
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