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 journalArticlepeer-review

58 Citations (Scopus)


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
Issue number21
Publication statusPublished - 2012 May 27


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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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