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Comptes Rendus Chimie
Sous presse. Epreuves corrigées par l'auteur. Disponible en ligne depuis le dimanche 6 octobre 2019
Doi : 10.1016/j.crci.2019.09.002
Received : 26 August 2019 ;  accepted : 3 September 2019
New functionalized scaffolds from hydroxymethylfurfural and glucosyloxymethylfurfural by Morita–Baylis–Hillman reaction with cycloalkenones
Nouveaux squelettes fonctionnalisés issus de l'hydroxyméthylfurfural et du glucosyloxyméthylfurfural par réaction de Morita–Baylis–Hillman avec des cycloalcénones
 

Lianjie Wang a, 1, Jia-Neng Tan b, 1, Mohammed Ahmar a, Yves Queneau a,
a Université de Lyon, Institut de chimie et biochimie moléculaires et supramoléculaires, ICBMS, UMR 5246 CNRS, Université Lyon-1, INSA de Lyon, CPE Lyon, Bâtiment Edgar-Lederer, 1, rue Victor-Grignard, 69622 Villeurbanne cedex, France 
b Tobacco Research Institute of the Chinese Academy of Agricultural Sciences, Qingdao 266101, PR China 

Corresponding author.
Abstract

New highly functionalized scaffolds, namely 2-(2-furyl)hydroxymethyl-2-cycloalkenones, are reported. The access to these systems is one step using an aqueous Morita–Baylis–Hillman reaction combining hydroxymethylfurfural and glucosyloxymethylfurfural and cycloalkenones for which the reaction conditions (promoter, solvent, concentration, and stoichiometry) have been optimized.

The full text of this article is available in PDF format.
Résumé

De nouvelles architectures fonctionnalisées de type 2-(2-furyl)hydroxyméthyl-2-cycloalcénone sont décrites. L'accès à ces systèmes se fait en une seule étape par réaction de Morita–Baylis–Hillman (MBH) dans l'eau associant le HMF ou le GMF avec des cycloalcénones, pour laquelle les conditions (promoteur, concentration, stœchiométrie) ont été optimisées.

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Highlights

New structures arising from cycloalkenones with hydroxymethylfurfural (HMF) and glucosyloxymethylfurfural (GMF) in Baylis–Hillman reactions.
High-level of functionality in one step.
Contribution to widening the scope of uses of HMF and GMF in fine chemistry.
First use of HMF and GMF in cycloalkenone–Morita-Baylis-Hillman reactions.
One-step, mild and clean conditions.

The full text of this article is available in PDF format.

Keywords : Cycloalkenones, HMF, GMF, Morita–Baylis–Hillman reaction

Motsclés : Cycloalcénones, HMF, GMF, Réaction de Morita–Baylis–Hillman


1  These authors contributed equally to this work.


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