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Concept
Kinetic resolution
Summary
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. 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.
The first reported kinetic resolution was achieved by Louis Pasteur. After reacting aqueous racemic ammonium tartrate with a mold from Penicillium glaucum, he reisolated the remaining tartrate and found it was levorotatory. The chiral microorganisms present in the mold catalyzed the metabolization of (R,R)-tartrate selectively, leaving an excess of (S,S)-tartrate.
Kinetic resolution by synthetic means was first reported by Marckwald and McKenzie in 1899 in the esterification of racemic mandelic acid with optically active (−)-menthol. With an excess of the racemic acid present, they observed the formation of the ester derived from (+)-mandelic acid to be quicker than the formation of the ester from (−)-mandelic acid. The unreacted acid was observed to have a slight excess of (−)-mandelic acid, and the ester was later shown to yield (+)-mandelic acid upon saponification.
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