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Issue 2, 2015
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Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications

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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

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Article information


Submitted
03 Oct 2014
Accepted
30 Oct 2014
First published
30 Oct 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 1043-1048
Article type
Edge Article
Author version available

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

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