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

doi:10.1039/c4sc03047h

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

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1043-1048
Number of pages	6
Journal	Chemical Science
Volume	6
Issue number	2
DOIs	https://doi.org/10.1039/c4sc03047h
Publication status	Published - 2015 Feb 1

ASJC Scopus subject areas

Chemistry(all)

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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.",

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

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AU - Maeno, Mayaka

AU - Tokunaga, Etsuko

AU - Yamamoto, Takeshi

AU - Suzuki, Toshiya

AU - Ogino, Yoshiyuki

AU - Ito, Emi

AU - Shiro, Motoo

AU - Asahi, Toru

AU - Shibata, Norio

PY - 2015/2/1

Y1 - 2015/2/1

N2 - 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.

AB - 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.

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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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