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Synthèse de composés β2,3-hydroxy- et aminocarboxylés par réactions domino et multicomposants métallo-catalysées

Abstract : The elaboration of metallo-catalyzed multicomponent reactions contributes to the development of a greener chemistry. Indeed, the association of multicomponent reactions with catalysis, through the limitation of the number of reaction steps and the use of toxic reagents, allows to increase the eco-compatibility of a process.The application of these principles has enabled the cobalt-catalyzed synthesis of β2,3-hydroxy- et β2,3-aminocarboxylated derivatives, compounds of increasing interest in medicinal chemistry, starting from halogenated derivatives, Michael acceptors and aldehydes or imines.In a first part, the reaction conditions have been optimized and the scope of the reaction has then been studied to demonstrate its generality. Moreover, stereochemical and mechanistical studies have been realized by the use of chiral auxiliaries or catalysts in the reaction. The valorization of the prepared compounds has also been undertaken in post-condensation reactions in particular for the synthesis of heterocycles. The multicomponents reaction developed during this work has finally been extended to the elaboration of new reactivities, thus contributing to spread the use of cobalt in organic chemistry
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Jérôme Paul. Synthèse de composés β2,3-hydroxy- et aminocarboxylés par réactions domino et multicomposants métallo-catalysées. Matériaux. Université Paris-Est, 2017. Français. ⟨NNT : 2017PESC1167⟩. ⟨tel-01789699⟩

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