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Synthèse énantiosélective d’1,2 et 1,3-diamines et Développement de réactions multicomposants dans des conditions oxydantes

Abstract : The aim of this study is the development of new access to highly functionalized nitrogen-containing compounds with respect to the green chemistry principles.First, an Ugi four-component reaction from alcohols has been studied. In the presence of hypervalent iodine compounds, used as oxidant and introduced in stoechiometric or catalytic quantites, an efficient one-pot sequence has been developed.Then, a new four-component Mannich reaction using a catalytic amount of BINOL-derived phosphoric acid gave an access to enantioenriched 1,3-diamines from enamides. Changing the electrophilic imine partner to a diazene compound afforded aminoketones or 1,2-diamines precursors in high yields and excellent enantiomeric excess.Finally, two new iron-catalyzed multicomponent reactions of enamides with TEMPO and various nucleophiles provided an efficient synthesis of aminoalcohols derivatives. These domino reactions involving an oxidative process from enamides offered a convenient and economical method to establish two C-O bonds in a single operation.
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Fleur Drouet. Synthèse énantiosélective d’1,2 et 1,3-diamines et Développement de réactions multicomposants dans des conditions oxydantes. Autre. Université Paris Sud - Paris XI, 2011. Français. ⟨NNT : 2011PA112344⟩. ⟨tel-00823407⟩

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