Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application
| Autor: | Jean-Christophe Rouaud, Carole F. Despiau, Anne Boussonnière, Jacques Lebreton, Fabrice Dénès, Romain Bénéteau |
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| Přispěvatelé: | Cibles et médicaments de l'infection, de l'immunité et du cancer (IICiMed), Université de Nantes - UFR des Sciences Pharmaceutiques et Biologiques, Université de Nantes (UN)-Université de Nantes (UN), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2016 |
| Předmět: | |
| Zdroj: | Pure and Applied Chemistry Pure and Applied Chemistry, 2016, 88 (3), pp.215-225. ⟨10.1515/pac-2015-1203⟩ |
| ISSN: | 1365-3075 0033-4545 |
| DOI: | 10.1515/pac-2015-1203 |
| Popis: | We developed a new approach to γ-lactols and methylene-γ-lactols based upon the radical cyclization of aluminium acetals obtained by reduction of α-bromoesters with DIBAL-H. The cyclic aluminium acetals resulting from the cyclization process could engage in situ in further functionalization, as illustrated by the Oppenauer-type oxidation to give the corresponding lactones and γ-butenolides. The preparation of butenolides using this strategy compared favourably with the direct, tin-mediated cyclization of α-bromoesters, for which side reactions such as epimerization via [1,5]-HAT processes have been observed. |
| Databáze: | OpenAIRE |
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