Application of Axially Dissymmetric 1,1′-Binaphthyl Derivatives to Chiral Derivatizing Agents

Tetsutaro Hattori, Junichi Goto, Sotaro Miyano

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Axially dissymmetric 2′-methyl- and 2′-methoxy-1,1′-binaphthyl-2-carboxylic acid (1,2) were effectively utilized as chiral derivatizing agents for discrimination of enantiomeric alcohols and amines by high performance liquid chromatography (HPLC) on silica gel. Especially, 2 had excellent chirality-recognizing ability, and could also be utilized for discrimination by 1H NMR with the aid of Eu(fod)3. The elution behavior of a pair of diastereomeric esters or amides on HPLC, as well as the NMR behavior of the diastereomers were rationally explained based on X-ray crystallography analyses. Carbonyl cyanide derivatives of 1 and 2 were successfully applicable to resolution of β-adrenergic blocker enantiomers in biological fluids by HPLC. These diastereomeric esters were highly responsive to a fluorescence detector, the limit of detection being 200 pg and 30 pg (at a signal-to-noise ratio of 5), respectively. Also reported are convenient methods for the preparation of these reagents.

Original languageEnglish
Pages (from-to)986-996
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume50
Issue number11
DOIs
Publication statusPublished - 1992
Externally publishedYes

Keywords

  • 2′-Methoxy-1,1′-binaphthyl-2-carboxylic acid
  • 2′-Methyl-1,1′-binaphthyl-2-carboxylic acid
  • Chiral derivatizing agent
  • Enantiomeric alcohol
  • Enantiomeric amine
  • Fluorescence detection
  • H NMR
  • High performance liquid chromatography
  • β-Adrenergic blocker

ASJC Scopus subject areas

  • Organic Chemistry

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