Literature DB >> 23716267

Optical purifications via self-disproportionation of enantiomers by achiral chromatography: case study of a series of α-CF3-containing secondary alcohols.

Alexander E Sorochinsky1, Toshimasa Katagiri, Taizo Ono, Alicja Wzorek, José Luis Aceña, Vadim A Soloshonok.   

Abstract

This work demonstrates that self-disproportionation of enantiomers via achiral chromatography can be recommended as inexpensive and general method for optical purification of enantiomerically enriched compounds. In particular, the advantage of this approach over conventional recrystallization is that it can be used for both crystalline as well as liquid compounds.
© 2013 Wiley Periodicals, Inc.

Entities:  

Year:  2013        PMID： 23716267     DOI： 10.1002/chir.22180

Source DB:  PubMed          Journal:  Chirality        ISSN： 0899-0042            Impact factor:   2.437


  10 in total

Review 1.  Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives.

Authors:  Jianlin Han; Jorge Escorihuela; Santos Fustero; Aitor Landa; Vadim A Soloshonok; Alexander Sorochinsky
Journal:  Molecules       Date:  2022-06-13       Impact factor: 4.927

Review 2.  Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs.

Authors:  Yi Zhu; Jianlin Han; Jiandong Wang; Norio Shibata; Mikiko Sodeoka; Vadim A Soloshonok; Jaime A S Coelho; F Dean Toste
Journal:  Chem Rev       Date:  2018-04-02       Impact factor: 60.622

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

Authors:  Mayaka Maeno; Etsuko Tokunaga; Takeshi Yamamoto; Toshiya Suzuki; Yoshiyuki Ogino; Emi Ito; Motoo Shiro; Toru Asahi; Norio Shibata
Journal:  Chem Sci       Date:  2014-10-30       Impact factor: 9.825

Review 4.  The self-disproportionation of enantiomers (SDE): a menace or an opportunity?

Authors:  Jianlin Han; Osamu Kitagawa; Alicja Wzorek; Karel D Klika; Vadim A Soloshonok
Journal:  Chem Sci       Date:  2018-01-15       Impact factor: 9.825

5.  Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles.

Authors:  Ziyi Li; Li Wang; Yunqi Huang; Haibo Mei; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok; Jianlin Han
Journal:  Beilstein J Org Chem       Date:  2020-10-29       Impact factor: 2.883

Review 6.  The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine.

Authors:  Qian Wang; Jianlin Han; Alexander Sorochinsky; Aitor Landa; Greg Butler; Vadim A Soloshonok
Journal:  Pharmaceuticals (Basel)       Date:  2022-08-14

Review 7.  Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions.

Authors:  Jianlin Han; Alicja Wzorek; Karel D Klika; Vadim A Soloshonok
Journal:  Molecules       Date:  2021-05-07       Impact factor: 4.411

8.  Biological evaluation of both enantiomers of fluoro-thalidomide using human myeloma cell line H929 and others.

Authors:  Etsuko Tokunaga; Hidehiko Akiyama; Vadim A Soloshonok; Yuki Inoue; Hideaki Hara; Norio Shibata
Journal:  PLoS One       Date:  2017-08-01       Impact factor: 3.240

9.  Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers.

Authors:  Etsuko Tokunaga; Takeshi Yamamoto; Emi Ito; Norio Shibata
Journal:  Sci Rep       Date:  2018-11-20       Impact factor: 4.379

10.  Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid.

Authors:  Jianlin Han; Ryosuke Takeda; Xinyi Liu; Hiroyuki Konno; Hidenori Abe; Takahiro Hiramatsu; Hiroki Moriwaki; Vadim A Soloshonok
Journal:  Molecules       Date:  2019-12-10       Impact factor: 4.411
  10 in total

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