Institut de Chimie Moléculaire et des Matériaux d'Orsay

Laboratoire de Catalyse Moléculaire - LCM


Equipe de Catalyse Moléculaire-ICMMO - Bât 420
Université Paris-Sud 11
15, rue Georges Clemenceau
91405 Orsay Cedex

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1. Functionalized Chiral Ionic Liquids (FCILs)

[Giang Vo-Thanh (Prof.), Audrey Aupoix, Thu Truong (Ph.D students) (Developed in 2005)]

We have designed and synthesized some new families of FCILs derived from naturally biorenewable sources (natural amino acids, carbohydrates,…). These FCILs could be used as new chiral reaction media (chiral solvent and/or organocatalyst) for asymmetric synthesis and catalysis.

Example: asymmetric Michael addition.Tetrahedron 2010, 66, 5277


2. Synthesis of multidentate ligands for enantioselective catalysis

[Giang Vo-Thanh (Prof.), Martial Toffano (Researcher, CNRS), Chloée Bournaud (Assistant Prof.), Houssein Ibrahim, Khanh-Duy Huynh (Ph.D students)] (Developed in 2007)

A new class of ß-amino alcohol, diamine and phosphine ligands has been prepared from isosorbide and isomannide as chiral renewable sources. The efficiency of these ligands has been evaluated for metal-catalyzed enantioselective reactions (e.g: C-C, C-N bonding formations).

Example: olefin enantioselective hydrogenation using monophosphine ligand.
Tetrahedron: Asymmetry,
2010, 21, 1542; New. J. Chem. 2011, 35, 2622



3. Chiral N-Heterocyclic Carbenes (NHC)

[Giang Vo-Thanh (Prof.), Chloée Bournaud (Assistant Prof.), Martial Toffano (Researcher, CNRS), Audrey Aupoix, Amélia Thomasset (Ph.D students) Sophia Berkani (Ms)](Developed in 2007)

We have developed a new and flexible procedure for the synthesis of chiral azolium salts, precursors to N-heterocyclic carbenes, derived from (S)-pyroglutamic acid. The efficiency of these NHCs has been evaluated in asymmetric catalysis (organic and organometallic catalysis).

Example: asymmetric reduction of aromatic ketones by transfer hydrogenation using chiral NHC ligand (highest enantioselectivity to date for a transfer hydrogenation catalysts incorporating a chiral NHC ligand). Eur. J.Org. Chem., 2011, 2772.



4. Organocatalysis

[Giang Vo-Thanh (Prof.), Martial Toffano (Researcher, CNRS), Chloée Bournaud (Assistant Prof.), Houssein Ibrahim (Ph.D student), Delphine Kalch (Postdoctoral Associate)](Research topic developed in 2010)

a. Some monophosphines derived from isosorbide and isomannide were evaluated as organocatalysts for [3+2] cyclisation reaction giving good diastereoselectivity and moderate enantioselectivity. Some modifications of phosphines structure are envisaged. It should allow to improving the enantioselectivity of this reaction (in collaboration with Dr. A. Marinetti’s group).


b. Some ureas and thio-ureas have been synthesized and evaluated as organocatalysts in the Friedel-Crafts reaction of indol with nitrostyrene affording good conversion but with moderate asymmetric induction for a moment. The work is currently in progress in our group.


5. Asymmetric synthesis under microwaves activation at low temperature

[Giang Vo-Thanh (Prof.), Martial Toffano (Researcher, CNRS), Chloée Bournaud (Assistant Prof.), Delphine Kalch (Postdoctoral Associate)](New topic developed in 2011)

This research topic is developed in collaboration with CEM Company.

6. 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 in Bratislava, Slovakia, 2009-2102).

The main aim of ongoing project was the development of an alternative catalytic systems for Pd(II)-catalyzed oxycarbonylation reaction in essential effort to improve the enantioselectivity comparing to results reported in literature (Kapitan P. et al. Arkivoc, 2008, 8, 8-17). Our work consists in studying this asymmetric reaction by varying several parameters, in particular, chiral ligand screening, the exploration of alternative reoxidant systems, the investigation of possible solvent or temperature influence, and to test the suitability of green solvents such as ionic liquids or chiral ionic liquids for our target transformation. The first results obtained are presented in following Scheme.

Example: asymmetric intramolecular palladium (II)-catalyzed oxycarbonylation (best result has been reported so far)



7. Synthesis and applications of new sulfoximines

[Giang Vo-Thanh (Prof.), Martial Toffano (Researcher, CNRS), Chloée Bournaud (Assistant Prof.), Yohan Macé (Postdoctoral Associate)] (In collaboration with Dr. E. Magnier‘s group)

We have developed a simple and versatile system for copper-catalyzed N-arylation of fluorinated sulfoximines giving excellent yields. This innovative process allows a new and low cost access to a large panel of N-arylated fluoroalkylated sulfoximines. These sulfoximines could be used as ligand for organometallic catalysis. This work is currently underway in our Lab.

Example: Copper-Induced coupling between NH-fluoroalkylated Sulfoximines and Aryl Iodides or Bromides Tetrahedron 2011, 67, 7575


8. Enantioselective total synthesis of Sphingofungine (antifungal activity)

(New project developed in 2012)