Amplification of the enantiomeric excess of a compound in kinetic resolution by a racemic reagent

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...

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Bibliographic Details
Published in:Tetrahedron 2007-07, Vol.63 (28), p.6415-6422
Main Authors: Satyanarayana, Tummanapalli, Kagan, Henri B.
Format: Article
Language:English
Subjects:
Asymmetric amplification
Biomolecular homochirality
Enantioenrichment
Kinetic resolution
Racemic reagent
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.03.077