From a Racemate to a Single Enantiomer: Deracemization by Stereoinversion

Authors

  • Christian C. Gruber,

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria Fax: (+43)-316-380-9840
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  • Iván Lavandera,

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria Fax: (+43)-316-380-9840
    2. Research Centre Applied Biocatalysis, Graz, Austria
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  • Kurt Faber,

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria Fax: (+43)-316-380-9840
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  • Wolfgang Kroutil

    1. Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria Fax: (+43)-316-380-9840
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Abstract

The stereoinversion of one enantiomer into its mirror-image counterpart within a racemate furnishes a single stereoisomeric product in 100 % theoretical yield. This extremely efficient type of deracemization, whereby substrate and product possess an identical chemical structure, can be achieved by using bio- or chemo-catalysts or combinations thereof and is applicable to secondary alcohols, amines and α-substituted carboxylic acids. Special emphasis is devoted to the theoretical background of the one-pot, single-step deracemization of sec-alcohols.

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