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

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43 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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Nakamura, T., Tateishi, K., Tsukagoshi, S., Hashimoto, S., Watanabe, S., Soloshonok, V. A., Aceña, J. L., & 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