Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications. Issue 2 (14th November 2014)

• Record Type: Journal Article
• Authors: Maeno, Mayaka; Tokunaga, Etsuko; Yamamoto, Takeshi; Suzuki, Toshiya; Ogino, Yoshiyuki; Ito, Emi; Shiro, Motoo; Asahi, Toru; Shibata, Norio
• Is Part Of: Chemical science. Volume 6:Issue 2(2015:Feb.)
• Page Start: 1043
• Page End: 1048
• Publication Date: 2014-11-14
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c4sc03047h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We report on the self-disproportionation of enantiomers of non-racemic thalidomide (1 ) and 3′-fluorothalidomide (2 ) under achiral chromatography. 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 of1 and2, resulting in the opposite SDE profile on silica-gel.