Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography

Tsuyoshi Nakamura, Kaori Tateishi, Shiori Tsukagoshi, Saori Hashimoto, Shotaro Watanabe, Vadim A. Soloshonok, José Luis Aceña, Osamu Kitagawa

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Efficient self-disproportionation of enantiomers of several non-racemic chiral amines was achieved through conversion to N-acetamides and subsequent MPLC using an achiral column. The MPLC of these non-racemic N-acetamide derivatives gave the chart having a clear boundary between two fractions. Thus, in the less polar fraction, remarkable enantiomer enrichment was observed (>99%ee), while the ee of more polar fraction was considerably reduced. The magnitude of the enantiomer enrichments and depletions strongly depended on substituent on the amino group.

Original languageEnglish
Pages (from-to)4013-4017
Number of pages5
JournalTetrahedron
Volume68
Issue number21
DOIs
Publication statusPublished - 2012 May 27

Fingerprint

Enantiomers
Chromatography
Amines
Derivatives
Acetamides

Keywords

  • Chromatography
  • Enantiomers
  • Enrichment
  • Phenylethylamines
  • Self-disproportionation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Nakamura, T., Tateishi, K., Tsukagoshi, S., Hashimoto, S., Watanabe, S., Soloshonok, V. A., ... Kitagawa, O. (2012). Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography. Tetrahedron, 68(21), 4013-4017. https://doi.org/10.1016/j.tet.2012.03.054

Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography. / Nakamura, Tsuyoshi; Tateishi, Kaori; Tsukagoshi, Shiori; Hashimoto, Saori; Watanabe, Shotaro; Soloshonok, Vadim A.; Aceña, José Luis; Kitagawa, Osamu.

In: Tetrahedron, Vol. 68, No. 21, 27.05.2012, p. 4013-4017.

Research output: Contribution to journalArticle

Nakamura, T, Tateishi, K, Tsukagoshi, S, Hashimoto, S, Watanabe, S, Soloshonok, VA, Aceña, JL & Kitagawa, O 2012, 'Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography', Tetrahedron, vol. 68, no. 21, pp. 4013-4017. https://doi.org/10.1016/j.tet.2012.03.054
Nakamura T, Tateishi K, Tsukagoshi S, Hashimoto S, Watanabe S, Soloshonok VA et al. Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography. Tetrahedron. 2012 May 27;68(21):4013-4017. https://doi.org/10.1016/j.tet.2012.03.054
Nakamura, Tsuyoshi ; Tateishi, Kaori ; Tsukagoshi, Shiori ; Hashimoto, Saori ; Watanabe, Shotaro ; Soloshonok, Vadim A. ; Aceña, José Luis ; Kitagawa, Osamu. / Self-disproportionation of enantiomers of non-racemic chiral amine derivatives through achiral chromatography. In: Tetrahedron. 2012 ; Vol. 68, No. 21. pp. 4013-4017.
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