Synthesis 2013; 45(2): 141-152
DOI: 10.1055/s-0032-1316812
review
© Georg Thieme Verlag Stuttgart · New York

Self-Disproportionation of Enantiomers of Chiral, Non-Racemic Fluoroorganic Compounds: Role of Fluorine as Enabling Element

Alexander E. Sorochinsky
a   Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain   Fax: +34 943015270   Email: vadym.soloshonok@ehu.es
b   IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain
c   Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street 1, Kyiv-94 02660, Ukraine
,
José Luis Aceña
a   Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain   Fax: +34 943015270   Email: vadym.soloshonok@ehu.es
,
Vadim A. Soloshonok*
a   Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastián, Spain   Fax: +34 943015270   Email: vadym.soloshonok@ehu.es
b   IKERBASQUE, Basque Foundation for Science, 48011 Bilbao, Spain
› Author Affiliations
Further Information

Publication History

Received: 06 October 2012

Accepted after revision: 24 October 2012

Publication Date:
16 November 2012 (online)


Abstract

This review discusses all available literature on the self-disproportionation of enantiomers (SDE) of fluorine-containing compounds, resulting in a separation of racemic form from the excess enantiomer. Included are examples of the SDE via distillation, sublimation and achiral chromatography. The role of fluorine on the magnitude and preparative efficiency of the SDE, as a new, nonconventional method for optical purifications, is emphasized and critically discussed.

1 Introduction

2 General Aspects of Fluorine Influence on the Self-Disproportionation of Enantiomers

3 Self-Disproportionation of Enantiomers via Distillation

4 Self-Disproportionation of Enantiomers via Sublimation

5 Self-Disproportionation of Enantiomers via Achiral Chromatography

6 Conclusions

 
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