Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application

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Abstract: 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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application ; volume:88 ; number:3 ; year:2016 ; pages:215-225 ; extent:11
Pure and applied chemistry ; 88, Heft 3 (2016), 215-225 (gesamt 11)

Creator: Boussonnière, Anne
Bénéteau, Romain
Rouaud, Jean-Christophe
Despiau, Carole
Lebreton, Jacques
Dénès, Fabrice

DOI: 10.1515/pac-2015-1203

URN: urn:nbn:de:101:1-2024030613185756208433

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 11:04 AM CEST

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Boussonnière, Anne
Bénéteau, Romain
Rouaud, Jean-Christophe
Despiau, Carole
Lebreton, Jacques
Dénès, Fabrice

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Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application

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Other Objects (12)

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A Persistent Phosphanyl‐Substituted Thioketyl Radical Anion

Chemoselective Post‐Synthesis Modification of Pyridyl‐Substituted, Aromatic Phosphorus Heterocycles: Cationic Ligands for Coordination Chemistry

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

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Non‐native Intramolecular Radical Cyclization Catalyzed by a B 12 ‐Dependent Enzyme **

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