Chiral Ionic Liquids: New reaction media (solvent and/or catalyst) for asymmetric synthesis and catalysis [Giang Vo-Thanh (Prof.), Audrey Aupoix,Thu Truong.

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Presentation transcript:

Chiral Ionic Liquids: New reaction media (solvent and/or catalyst) for asymmetric synthesis and catalysis [Giang Vo-Thanh (Prof.), Audrey Aupoix,Thu Truong (Ph.D students)] Example: Synthesis of functionalized chiral ammonium and imidazolium-based ionic liquids derived from (-)- ephedrine using solvent-free microwave activation. Applications for the asymmetric Michael addition Tetrahedron, 2010, 66, 5277 Asymmetric intramolecular palladium (II)-catalyzed oxycarbonylation reaction in the presence of ionic liquid [Giang Vo-Thanh (Prof.), Martial Toffano (Researcher, CNRS), Jana Dohanosova (Ph.D student)] (‘Cotutelle Thesis’ in collaboration with Prof. Tibor Gracza’s group, University of Sciences and Technology, Bratislava, Slovakia, ). Example: asymmetric intramolecular palladium (II)-catalyzed oxycarbonylation (best result has been reported so far)

Chiral azolium salts as precursors to N-Heterocyclic Carbenes for asymmetric catalysis: [Giang Vo-Thanh (Prof.), Chloée Bournaud (Assistant Prof.), Audrey Aupoix, Amélia Thomasset (Ph.D students)] Example: Asymmetric transfer hydrogenation of aromatic ketone using rhodium complexes of chiral N- heterocyclic carbenes derived from (S)-pyroglutamic acid (the best enantioselectivity reported so far for a transfer hydrogenation catalyst incorporating a chiral NHC ligand). Eur. J. Org. Chem., 2011, 2772 Organic synthesis under solvent-free microwaves activation conditions [Giang Vo-Thanh (Prof.), Audrey Aupoix (Ph.D student)] Example: Synthesis of imidazolium and pyridinium-based ionic liquids and applications of 1-alkyl-3-methyl imidazolium salts as pre-catalysts for the benzoin condensation using solvent-free microwave activation Tetrahedron, 2010,66, 1352

Synthesis of new chiral ligands derived from isosorbide and isomannide (biomass products) [Giang Vo-Thanh (Prof.), Martial Toffano (Researcher, CNRS), Chloée Bournaud (Assistant Prof.), Houssein Ibrahim, Khanh-Duy Huynh (Ph.D students), Delphine Kalch (Postdoctoral Associate)] Example: Asymmetric transfer hydrogenation of aromatic ketones with amino-alcohol ligand Tetrahedron: Asymmetry, 2010, 21, 1542 Example: Enantioselective hydrogenation with monophosphine ligand New Journal Chem (in press) Synthesis of new chiral ligands or/and organocatalysts derived from natural chirality sources. Applications for asymmetric catalysis [Giang Vo-Thanh (Prof.), Martial Toffano, Jérôme Hannedouche (Researchers, CNRS), Chloée Bournaud (Assistant Prof.), Huong Nguyen (Ph.D student) Work in progress