Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography: mechanistic rationale and implications†,10.1039/C4SC03047H

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

Mayaka Maeno,Etsuko Tokunaga,Takeshi Yamamoto,Toshiya Suzuki,Yoshiyuki Ogino,Emi Ito,Motoo Shiro,Toru Asahi,Norio Shibata

Chemical Science Pub Date : 10/30/2014 00:00:00 , DOI:10.1039/C4SC03047H

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.