Kinetic resolution when the chiral auxiliary is not enantiomerically pure:Normal and abnormal behavior

Kinetic resolutions with enantioimpure chiral auxiliaries (reagents or cata lysts) are considered, and a kinetic treatment for various rate laws is des cribed. A useful parameter, the apparent stereoselectivity factor, is defin ed and correlated to the enantiomeric excess of the chiral auxiliary. Devia tions from the regular laws are possible (asymmetric amplification or deple tion). These anomalies have their origins in the same phenomena that cause nonlinear effects in enantioselective catalysis. Asymmetric amplifications have been experimentally observed.