In organic chemistry, kinetic resolution is a means of differentiating two enantiomers in a racemic mixture. In kinetic resolution, two enantiomers react with different reaction rates in a chemical reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer.[1] As opposed to chiral resolution, kinetic resolution does not rely on different physical properties of diastereomeric products, but rather on the different chemical properties of the racemic starting materials. The enantiomeric excess (ee) of the unreacted starting material continually rises as more product is formed, reaching 100% just before full completion of the reaction. Kinetic resolution relies upon differences in reactivity between enantiomers or enantiomeric complexes.
Kinetic resolution can be used for the preparation of chiral molecules in organic synthesis. Kinetic resolution reactions utilizing purely synthetic reagents and catalysts are much less common than the use of enzymatic kinetic resolution in application towards organic synthesis, although a number of useful synthetic techniques have been developed in the past 30 years.[2]
- ^ Fiaud, J.C.; Kagan, H.B. (1988). "Kinetic Resolution". In Eliel, E.L.; Wilen, S.H. (eds.). Topics in Stereochemistry. Vol. 18. New York: John Wiley and Sons, Inc. pp. 249–340.
- ^ Robinson, D.E.J.E.; Bull, S.D. (2005). "Kinetic resolution strategies using non-enzymatic catalysts". Tetrahedron: Asymmetry. 14 (11): 1407–1446. doi:10.1016/S0957-4166(03)00209-X.