Synthesis of new calix[4]arene based chiral ligands bearing β-amino alcohol groups and their application in asymmetric transfer hydrogenation.

Adrien Quintard (1) , Ulrich Darbost (1) , Francis Vocanson (1) , S Pellet-Rostaing (1) , M. Lemaire (1)

1 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires

A new series of chiral calix[4]arenes bearing β-amino alcohol groups have been synthesized. The crucial steps consisted on the binding of glycidyl groups on the lower rim of the calix[4]arenes followed by their regioselective opening with amines. Those ligands were successfully tested in asymmetric transfer hydrogenation. The best results (conversion max = 97% and ee max = 87%) were obtained using calix[4]arene mono-functionalized ligands. Those results are the best ones obtained using calixarenes based ligands in asymmetric catalysis.

Domaines: Matériaux

Adrien Quintard, Ulrich Darbost, Francis Vocanson, S Pellet-Rostaing, M. Lemaire. Synthesis of new calix[4]arene based chiral ligands bearing β-amino alcohol groups and their application in asymmetric transfer hydrogenation.. Tetrahedron: Asymmetry, 2007, 18, pp.1926. ⟨ujm-00351471⟩