Synthesis and properties of thiazoline based ionic liquids derived from the chiral pool
A novel class of chiral ionic liquids derived from amino alcohols is prepared in multi-gram scale. Their potential in chiral recognition is shown in a preliminary example with racemic Mosher's acid salt.
(N,N) vs. (N,S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study
New thiazoline-containing ligands including non-symmetric bis(thiazolines) and oxazoline-thiazolines were synthesized and then compared to C2-symmetric bis(thiazolines) in the palladium-catalyzed allylic substitution. The experimental results obtained in this study support the hypothesis of a competition between the (N,N) and the (N,S) palladium chelation, when sterically hindered bis(thiazolines) are used as ligands. A quantum chemical study performed on the Pd-complexes derived from three selected ligands, two C2-symmetric bis(thiazolines) and one oxazoline-thiazoline, also supports this hypothesis.
Synthesis of new chiral thiazoline-containing ligands
New chiral ligands, including bi- and tridentate thiazoline derivatives, analogues of known oxazolines, have been synthesized by a general and convenient procedure, starting from dithioesters and commercial enantiopure 2-aminoalcohols. A preliminary test shows the ability of such ligands to act as asymmetric catalysts in Pd-catalyzed allylic substitution reaction.