Jump to main content
Jump to site search

Issue 2, 2015
Previous Article Next Article

Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications

Author affiliations

Abstract

We report on the self-disproportionation of enantiomers (SDE) of non-racemic thalidomide (1) and 3′-fluorothalidomide (2) under the conditions of gravity-driven achiral silica-gel chromatography. The presence of a fluorine atom on the chiral center dramatically alters the structure and polarity of 1 and 2, resulting in the opposite SDE profile on silica-gel.

Graphical abstract: Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications

Back to tab navigation

Supplementary files

Publication details

The article was received on 03 Oct 2014, accepted on 30 Oct 2014 and first published on 30 Oct 2014


Article type: Edge Article
DOI: 10.1039/C4SC03047H
Citation: Chem. Sci., 2015,6, 1043-1048
  • Open access: Creative Commons BY license
  •   Request permissions

    Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications

    M. Maeno, E. Tokunaga, T. Yamamoto, T. Suzuki, Y. Ogino, E. Ito, M. Shiro, T. Asahi and N. Shibata, Chem. Sci., 2015, 6, 1043
    DOI: 10.1039/C4SC03047H

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements