Parallel kinetic resolution of active esters using a quasi-enantiomeric combination of ( R)-4-phenyl-oxazolidin-2-one and ( S)-4,5,5-triphenyl-oxazolidin-2-one

Abstract

The parallel kinetic resolution of a series of racemic pentafluorophenyl 2-(4-aryl/phenyl)-propionates and -butanoates using a quasi-enantiomeric combination of ( R)-4-phenyl-oxazolidin-2-one and ( S)-4,5,5-triphenyl-oxazolidin-2-one is discussed. The levels of diastereoselectivity were excellent (86–98% de) leading to separable quasi-enantiomeric oxazolidin-2-one adducts in good yield. This methodology was used to resolve 2-phenyl propionic acid.