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L'alkylidène de l'acide de Meldrum comme plateforme utile en réaction multicomposés organocatalysée

Abstract : The purpose of this thesis was to access to chiral heterocycles such as isoxazolidin-5-ones by making use of an organocatalyzed multicomponent reaction involving significantly reactive intermediates, namely Meldrum’s acid alkylidenes. The use of unusual nucleophiles such as urea derivatives and a newly designed Cinchona alkaloids derived organocatalyst led us to the development of the first organocatalyzed enantioselective multicomponent Knoevenagel/aza-Michael/Cyclocondensation reaction giving access to β-substituted isoxazolidin-5-ones. We also developed a diastereoselective version of this reaction, making use of hydroxylamides derived from α-amino acid derivatives in order to synthesize isoxazolidin-5-ones containing the α-amino acid pattern. These platforms were exploited to open synthetic routes to biologically relevant compounds such as β-amino acid and α,β-dipeptide derivatives.
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Submitted on : Tuesday, May 17, 2022 - 10:53:20 AM
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  • HAL Id : tel-03420100, version 2

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Julien Annibaletto. L'alkylidène de l'acide de Meldrum comme plateforme utile en réaction multicomposés organocatalysée. Chimie organique. Normandie Université, 2019. Français. ⟨NNT : 2019NORMIR19⟩. ⟨tel-03420100v2⟩

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