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Elaboration de liquides ioniques (chiraux) réversibles et applications en catalyse organique et en glycochimie. Carbènes N-hétérocycliques chiraux : synthèse et application dans la réaction d'addition conjuguée

Abstract : At first, this work deals with the synthesis of a novel class of single-component reversible chiral ionic liquids derived from natural aminoacids. Reversibility was demonstrated by NMR, thermogravimetric analysis and differential scanning calorimetry. These compounds were tested as organocatalysts in an asymmetric Michael addition leading to the formation of expected product in moderate yields. Chiral silylamines, precursors to reversible ionic liquids were also evaluated in the synthesis of Warfarin through an asymmetric Michael addition. Good yields were obtained. However, these catalysts have resulted in only low enantioselectivity. Moreover, the use of reversible ionic liquid as a temporary protecting group in glycochemistry, for the synthesis of disaccharides was also implemented. Secondly, some new chiral imidazolinium salts, precursors to NHCs, were synthesized from (S)-pyroglutamic acid, for copper-catalyzed conjugate addition of Grignard reagents to α,β-unsaturated ketones applications. The results have shown moderate enantioselectivity with very good catalytic activity and excellent regioselectivity.
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Lucie Bouchardy. Elaboration de liquides ioniques (chiraux) réversibles et applications en catalyse organique et en glycochimie. Carbènes N-hétérocycliques chiraux : synthèse et application dans la réaction d'addition conjuguée. Chimie organique. Université Paris-Saclay, 2016. Français. ⟨NNT : 2016SACLS400⟩. ⟨tel-01683248⟩

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