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Synthèse de nouveaux catalyseurs bifonctionnels peptidiques incluant un motif acide phosphonique pour la création de liaisons C-C énantiosélective

Abstract : A novel bifunctional organocatalyst library combining both aminocatalysis and phosphonic acid activation on a peptide structure was developed. Some structural variations allowed the optimization of the catalytic site. The potential of these catalysts was evaluated on the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes. In optimized conditions, very good selectivities (up to 95:5 d.r. and 93:7 e.r) were achieved. Due to their high water-solubility, the catalysts were easily recyclable and reused over several cycles without any significant loss of selectivities. Mechanistic investigations were carried out to understand the exact mode of action of the catalysts. Both enamine formation and acid activation were essential for the reaction to occur. The peptide structure allows an intramolecular and stereoselective reaction.
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https://tel.archives-ouvertes.fr/tel-01684736
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Submitted on : Monday, January 15, 2018 - 5:11:49 PM
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Margery Cortes-Clerget. Synthèse de nouveaux catalyseurs bifonctionnels peptidiques incluant un motif acide phosphonique pour la création de liaisons C-C énantiosélective. Catalyse. Université Sorbonne Paris Cité, 2015. Français. ⟨NNT : 2015USPCD058⟩. ⟨tel-01684736⟩

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