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Self-disproportionation of Enantiomers of Enantiomerically Enriched Compounds

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Differentiation of Enantiomers II

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 341))

Abstract

This review describes self-disproportionation of enantiomers (SDE) of non-racemic mixtures, subjected to distillation, sublimation, or chromatography on achiral stationary phase using achiral eluent, which leads to the substantial enantiomeric enrichment and corresponding depletion in different fractions, as compared to the enantiomeric composition of the starting material. This phenomenon is of a very general nature as SDE has been reported for different classes of chiral organic compounds bearing various functional groups and possessing diverse elements of chirality. The literature data discussed in this review clearly suggests that SDE is typical for enantiomerically enriched chiral organic compounds and special care should always be taken in evaluation of the stereochemical outcome of enantioselective reactions as well as determination of enantiomeric ratios of non-racemic mixtures of natural products after any purification process. The role of molecular association of enantiomers on the magnitude and preparative efficiency of SDE, as a new, nonconventional method for enantiomerc purifications, is emphasized and discussed.

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Abbreviations

MOM:

Methoxymethyl

PMB:

4-Methoxyphenyl

SEC:

Size-exclusion chromatography

Tol:

4-methylphenyl

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Authors and Affiliations

  1. Faculty of Chemistry, Department of Organic Chemistry I, University of Basque Country UPV/EHU, 20018, San Sebastian, Spain

    Alexander E. Sorochinsky

  2. IKERBASQUE, Basque Foundation for Science, 48011, Bilbao, Spain

    Vadim A. Soloshonok

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  1. Alexander E. Sorochinsky
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Correspondence to Vadim A. Soloshonok .

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  1. Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany

    Volker Schurig

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Sorochinsky, A.E., Soloshonok, V.A. (2013). Self-disproportionation of Enantiomers of Enantiomerically Enriched Compounds. In: Schurig, V. (eds) Differentiation of Enantiomers II. Topics in Current Chemistry, vol 341. Springer, Cham. https://doi.org/10.1007/128_2013_434

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