Journal
TETRAHEDRON
Volume 63, Issue 28, Pages 6415-6422Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.03.077
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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. (c) 2007 Elsevier Ltd. All rights reserved.
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