Synthesis of Quinoline-Oxazolines and Investigation of their Catalytic Activity and Stereoselectivity

Abstract:

This research was designed to prepare new chiral quinoline-oxazolines with different substituents on the quinoline ring in order to investigate their catalytic activity and stereoselectivity of the zinc-catalyzed alkylation. The two quinoline-oxazolines that were prepared were 2-(5-hydro-4-phenyl-1,3-oxazol-2-yl)quinoline and 2-(5-hydro-4-phenyl-1,3-oxazol-2-yl) 6-methoxyquinoline, which were reacted with diethylzinc and

p-tolualdehyde to produce a enatiomeric mixture of 1-(4-methylphenyl)propan-1-ol. After purification through column chromatography ¹H-NMR was used to analyze the products. The enantiomeric excess of the product 1-(4-methylphenyl)propan-1-ol was determined to be close to 100% using the ¹H-NMR shift reagent Eu(hfc)₃.