Abstract:

Economical and efficient synthetic design of optically active chiral ligands for highly enantioselective transformations continue to be one of the most challenging tasks in asymmetric synthesis. The 2-oxazoline ring can be found in biologically active natural products and pharmaceuticals. In addition their chiral derivatives are widely used as ligands or chiral pools in asymmetric synthesis. There are a myriad of reactions and transformations stereoselectivilly-assisted by chiral oxazolines as for instance lactone synthesis, cyclopropanation, aziridination, Diels-Alder cycloaddition, allylic substitution, among others. In face of its large application, the development of practical, economically attractive as well as environmental benign methods to prepare 2- oxazolines is constantly desirable. In this work we describe a one-pot procedure to prepare 2-pyridil-2-oxazolines by reacting 2-cyanopyridine with chiral amino alcohols catalyzed by zinc acetate under pressure.