ICMUB - News

Vendredi 7 mars 2008 : Conf d'Armin Börner, Université de Rostock (Allemagne)

Some new developments in the homogeneously catalyzed asymmetric hydrogenation

Due its importance for industrial application the asymmetric hydrogenation with homogeneous Rh-, Ru- and Ircatalysts is still in the focus of academic research. In the contribution some recent developments in ligand design, hydrogenation of new substrates and total synthesis of pharmacologically important compounds will be reviewed. In the first part emphasis will be given to the modular synthesis of chiral phospholane ligands and the elucidation of structure-enantioselectivity relationship in catalysts with bidentate or self-associating monodentate ligands. The influence of electronic and steric effects (bite angle) will be analysed in detail. Proof will be given that the catalytic performance of self-associating catalysts can be dramatically affected by solvents (e.g. fluorinated alcohols). In the second part the advantage of the “forgotten” and “green” solvent propylencarbonate will be highlighted by means of some hydrogenation reactions. In the third part the application of commercially available ligands for the highly enantioselective hydrogenation of β-acetamido vinylphosphonates will be detailed. A new self-breeding system of a chiral catalyst is likewise presented. Finally, the application of the Ru-catalyzed asymmetric hydrogenation of β-keto esters is exemplarily shown in the framework of the total synthesis of the cholesterol lowering drugs Atorvastatine and Rosuvastatine, respectively.

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Contact : Sylvain Jugé

 

ICMUB (UMR 5260) - University of Burgundy - Dijon (France)