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Catalyse asymétrique en présence de complexes d'or(I) - Un nouvel arsenal pour la construction d'architectures moléculaires

Abstract : Over the last years, gold catalysis has gained considerable significance in organic synthesis, since it comprises atom-economic and highly efficient processes for the transformation of relatively simple substrates into valuable, highly complex molecular architectures. Despite these outstanding advances, the enantioselective variants have not flourished as fast and remain a highly challenging task. This project intends to address some technological barriers and contribute to fundamental research in the field of asymmetric cycloisomerization and domino reactions implying gold(I) and gold(III) catalytic systems, on a first approach, and highly modular chiral carbenic ligands. The ligands will be based on chiral N-Heterocyclic Carbenes (NHCs), as they represent a very effective and robust class of supporting ligands. More specifically, we will focus on the development of highly modular NHC architectures specifically designed to bring the chiral information in close proximity to the metallic center, which represents a key feature for an efficient asymmetric induction in gold catalysis. The target substrates of catalysis will be divided in two main classes, namely the 1,n-enynes and the unsaturated carbonyl/imino derivatives, since their gold(I)- and gold(III)-catalyzed conversion will afford a great molecular complexity. By taking advantage of the different reactivities and catalytic profiles of the NHC-Au(I) and NHC-Au(III) complexes, along with their silver counterparts, this project will allow the elaboration of a complete panel of efficient, general and unprecedented enantioselective catalytic systems towards the preparation of bio-relevant building blocks, precursors of natural products and biologically active molecules.
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Yue Tang. Catalyse asymétrique en présence de complexes d'or(I) - Un nouvel arsenal pour la construction d'architectures moléculaires. Autre. Université Paris sciences et lettres, 2019. Français. ⟨NNT : 2019PSLEC038⟩. ⟨tel-03510215⟩

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