Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implicationsElectronic supplementary information (ESI) available. CCDC 1009504, 1009505, 1009506, 1009507, 1009508, 1009509. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc03047h

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...

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Main Authors: Maeno, Mayaka, Tokunaga, Etsuko, Yamamoto, Takeshi, Suzuki, Toshiya, Ogino, Yoshiyuki, Ito, Emi, Shiro, Motoo, Asahi, Toru, Shibata, Norio
Format: Article
Language:English
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Summary: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. We report on the self-disproportionation of enantiomers of non-racemic thalidomide ( 1 ) and 3′-fluorothalidomide ( 2 ) under achiral chromatography.
ISSN:2041-6520
2041-6539
DOI:10.1039/c4sc03047h