One-Pot Synthesis of (+)-Nootkatone via ...
Type de document :
Article dans une revue scientifique
DOI :
URL permanente :
Titre :
One-Pot Synthesis of (+)-Nootkatone via Dark Singlet Oxygenation of Valencene: The Triple Role of the Amphiphilic Molybdate Catalyst
Auteur(s) :
Hong, Bing [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Lebeuf, Raphael [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Delbaere, Stephanie [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Laboratoire de Spectrochimie et Raman (LASIR) - UMR 8516
Alsters, Paul [Auteur]
Chemelot Innovation and Learning Labs (Geleen, Pays-Bas)
Rataj, Véronique [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Lebeuf, Raphael [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Delbaere, Stephanie [Auteur]
Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 [LASIRE]
Laboratoire de Spectrochimie et Raman (LASIR) - UMR 8516
Alsters, Paul [Auteur]
Chemelot Innovation and Learning Labs (Geleen, Pays-Bas)
Rataj, Véronique [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Titre de la revue :
Catalysts
Numéro :
6
Pagination :
184
Éditeur :
MDPI
Date de publication :
2016-12-26
ISSN :
2073-4344
Discipline(s) HAL :
Chimie/Chimie organique
Résumé en anglais : [en]
Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: ...
Lire la suite >Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: (i) singlet oxygenation of valencene according to the ene reaction; (ii) Schenck rearrangement of one hydroperoxide into the secondary β-hydroperoxide; and (iii) dehydration of the hydroperoxide into the desired (+)-nootkatone. The solvent effect on the hydroperoxide rearrangement is herein discussed. The amphiphilic dimethyldioctyl ammonium molybdate, which is also a balanced surfactant, played a triple role in this process, as molybdate ions catalyzed at both Step 1 and Step 3 and it allowed the rapid formation of a three-phase microemulsion system that highly facilitates product recovery. Preparative synthesis of the high added value (+)-nootkatone was thus performed at room temperature with an isolated yield of 46.5%. This is also the first example of a conversion of allylic hydroperoxides into ketones catalyzed by molybdate ions.Lire moins >
Lire la suite >Efficient one-pot catalytic synthesis of (+)-nootkatone was performed from (+)-valencene using only hydrogen peroxide and amphiphilic molybdate ions. The process required no solvent and proceeded in three cascade reactions: (i) singlet oxygenation of valencene according to the ene reaction; (ii) Schenck rearrangement of one hydroperoxide into the secondary β-hydroperoxide; and (iii) dehydration of the hydroperoxide into the desired (+)-nootkatone. The solvent effect on the hydroperoxide rearrangement is herein discussed. The amphiphilic dimethyldioctyl ammonium molybdate, which is also a balanced surfactant, played a triple role in this process, as molybdate ions catalyzed at both Step 1 and Step 3 and it allowed the rapid formation of a three-phase microemulsion system that highly facilitates product recovery. Preparative synthesis of the high added value (+)-nootkatone was thus performed at room temperature with an isolated yield of 46.5%. This is also the first example of a conversion of allylic hydroperoxides into ketones catalyzed by molybdate ions.Lire moins >
Langue :
Anglais
Audience :
Internationale
Vulgarisation :
Non
Établissement(s) :
ENSCL
CNRS
Centrale Lille
Univ. Artois
Université de Lille
CNRS
Centrale Lille
Univ. Artois
Université de Lille
Collections :
Équipe(s) de recherche :
Colloïdes catalyse oxydation (CÏSCO)
Date de dépôt :
2019-09-25T14:37:45Z
2022-11-16T08:26:32Z
2022-11-16T08:26:32Z
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