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Contrôle de la chiralité axiale par activation de liaisons C-H : accès à des molécules naturelles et ligands inédits

Abstract : Axial chirality is an important property of biologically active compounds, advanced materials and more importantly of ligands used in asymmetric catalysis. Indeed, numerous atropisomeric biaryls have demonstrated an excellent asymmetric induction capacity. Thus, the control of atropisomery and the development of original synthetic methodologies allowing the synthesis and the obtention of optically pure axially chiral compounds is an important goal for the scientific community. In this work, a new strategy for the synthesis of atropenriched axially chiral biaryls was explored. The use of enantiopur sulfoxides playing the role of both, a directing group and a chirality auxiliary, in a palladium catalyzed C-H functionalization, allowed the efficient construction of numerous highly atropenriched biaryl compounds. The developed methodologies were furthermore applied to the formal synthesis of an axially chiral and bioactive compound, (-)-steganone, as well as the synthesis of doubly atropisomeric unprecedented ligands. These ligands displayed an excellent potential for asymmetric induction in homogenous asymmetric hydrogenation.
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https://tel.archives-ouvertes.fr/tel-01911006
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Submitted on : Friday, November 2, 2018 - 11:13:07 AM
Last modification on : Thursday, July 11, 2019 - 3:44:02 PM
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Quentin Dherbassy. Contrôle de la chiralité axiale par activation de liaisons C-H : accès à des molécules naturelles et ligands inédits. Autre. Université de Strasbourg, 2017. Français. ⟨NNT : 2017STRAF069⟩. ⟨tel-01911006⟩

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