Amplification of the enantiomeric excess of a compound in kinetic resolution by a racemic reagent |
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Authors: | Tummanapalli Satyanarayana |
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Institution: | Laboratoire de Catalyse Moléculaire (UMR 8182, CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay, Université Paris-Sud, 91405 Orsay, France |
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Abstract: | The possibility of amplifying the small ee of a enantioimpure substance using a racemic reagent in kinetic resolution is discussed. A kinetic treatment of this problem along with some experimental proofs of the concept is presented. Simulation on kinetic resolution of small ee substrate by a racemic reagent showed an important enantioenrichment in the substrate ee, sometimes reaching close to absolute ee. Experiments of kinetic resolution of an amine of a small ee by a racemic acylating reagent gave a substantial amplification in ee of the amine. The possible transformation of an undetectable low ee in substrate to a detectable higher ee by using a suitable racemic reagent is also briefly discussed with help of calculations. The usefulness of asymmetric amplification by a racemic reagent is considered in the context of the biomolecular homochirality on earth. |
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Keywords: | Asymmetric amplification Enantioenrichment Kinetic resolution Racemic reagent Biomolecular homochirality |
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