Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0)

Abstract : This manuscript presents the development of novel palladium-catalysed [3+2] cycloaddition reactions between vinylcyclopropanes and various dipolarophiles. The first part of this work focused on the dearomatization of nitroaromatic compounds such as 3-nitroindoles and 2-nitrobenzofurans through a cycloaddition process with vinylcyclopropanes. In a second time, an enantioselective [3+2] cycloaddition of vinylcyclopropanes with α,β-unsaturated aldehydes under a synergistic metal-organocatalytic activation manifold was developed, leading to highly substituted cyclopentane scaffolds with very high enantioselectivity. In a third part of this work, the extension of this methodology towards the synthesis of heterocyclic compounds was investigated. A first approach dealing with the in situ generation of nitrogen-containing 1,3- and 1,4-dipoles did not lead to the desired reactivity, which prompted us to develop a palladium(0)-catalysed cycloaddition of vinylcyclopropanes and electron-deficient imines to synthesize pyrrolidine derivatives.
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Maxime Laugeois. Réactions de cycloadditions stéréosélectives originales reposant sur l'utilisation de vinylcyclopropanes électro-appauvris et la catalyse au palladium(0). Chimie organique. Université Pierre et Marie Curie - Paris VI, 2017. Français. ⟨NNT : 2017PA066353⟩. ⟨tel-02321201⟩

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