Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application
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.
- Standort
-
Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
-
Online-Ressource
- Sprache
-
Englisch
- Erschienen in
-
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)
- Urheber
-
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
- Rechteinformation
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
-
14.08.2025, 11:04 MESZ
Datenpartner
Dieses Objekt wird bereitgestellt von:
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Boussonnière, Anne
- Bénéteau, Romain
- Rouaud, Jean-Christophe
- Despiau, Carole
- Lebreton, Jacques
- Dénès, Fabrice
Ähnliche Objekte (12)
Vinylphosphonites for Staudinger-induced chemoselective peptide cyclization and functionalization
Oxidative radical ring-opening/cyclization of cyclopropane derivatives
Polycyclic Imines via Radical Cyclization of Ene Sulfonamides
Cyclization Reactions of Hydrazones XXVII* Synthesis and oxidative cyclization of some formazan-substituted quinoxaline-2-ones
‘Ligand-Free-Like’ CuCl-Catalyzed Atom Transfer Radical Cyclization of N-Substituted N-Allyl Polychloroamides to γ-Lactams
FAST AND CHEMOSELECTIVE N-DEBENZYLATION ROUTE TO CHIRAL 2-SUBSTITUTED THIOMORPHOLIN-3-ONES
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
Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay
Palladium‐Catalyzed Chemoselective Mono‐α‐Arylation of O‐Protected Hydroxyacetone with Ortho ‐Substituted (Hetero) aryl Electrophiles
Non‐native Intramolecular Radical Cyclization Catalyzed by a B 12 ‐Dependent Enzyme **
Vinylphosphonites for Staudinger-induced chemoselective peptide cyclization and functionalization
Oxidative radical ring-opening/cyclization of cyclopropane derivatives
Polycyclic Imines via Radical Cyclization of Ene Sulfonamides
Cyclization Reactions of Hydrazones XXVII* Synthesis and oxidative cyclization of some formazan-substituted quinoxaline-2-ones
‘Ligand-Free-Like’ CuCl-Catalyzed Atom Transfer Radical Cyclization of N-Substituted N-Allyl Polychloroamides to γ-Lactams
FAST AND CHEMOSELECTIVE N-DEBENZYLATION ROUTE TO CHIRAL 2-SUBSTITUTED THIOMORPHOLIN-3-ONES
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
Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay
Palladium‐Catalyzed Chemoselective Mono‐α‐Arylation of O‐Protected Hydroxyacetone with Ortho ‐Substituted (Hetero) aryl Electrophiles
Non‐native Intramolecular Radical Cyclization Catalyzed by a B 12 ‐Dependent Enzyme **
Vinylphosphonites for Staudinger-induced chemoselective peptide cyclization and functionalization
Oxidative radical ring-opening/cyclization of cyclopropane derivatives
Polycyclic Imines via Radical Cyclization of Ene Sulfonamides
Cyclization Reactions of Hydrazones XXVII* Synthesis and oxidative cyclization of some formazan-substituted quinoxaline-2-ones
‘Ligand-Free-Like’ CuCl-Catalyzed Atom Transfer Radical Cyclization of N-Substituted N-Allyl Polychloroamides to γ-Lactams
FAST AND CHEMOSELECTIVE N-DEBENZYLATION ROUTE TO CHIRAL 2-SUBSTITUTED THIOMORPHOLIN-3-ONES
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
Copper-catalyzed oxidative benzylic C-H cyclization via iminyl radical from intermolecular anion-radical redox relay
Palladium‐Catalyzed Chemoselective Mono‐α‐Arylation of O‐Protected Hydroxyacetone with Ortho ‐Substituted (Hetero) aryl Electrophiles