A simple quantitative chiral analysis of amino acid esters by fluorine-19 nuclear magnetic resonance using the modified James-Bull method

Chirality. 2019 Jan;31(1):34-40. doi: 10.1002/chir.23028. Epub 2018 Nov 5.

Abstract

A simple chiral analysis of amino acid esters by fluorine-19 nuclear magnetic resonance (19 F NMR) through the modified James-Bull method is described. Thus, amino acid ester acid salt was treated with 5-fluoro-2-formylphenylboronic acid and (S)-BINOL in the presence of triethylamine (TEA) and MS4A for 10 minutes. The reaction mixture was analysed by 19 F NMR directly to afford good quantifications.

Keywords: 19F NMR; James-bull assembly; amino acids; quantification.

MeSH terms

  • Amino Acids / analysis*
  • Amino Acids / chemistry
  • Benzaldehydes / chemistry
  • Esters / analysis*
  • Esters / chemistry
  • Ethylamines / chemistry
  • Fluorine
  • Magnetic Resonance Spectroscopy / methods*
  • Stereoisomerism

Substances

  • Amino Acids
  • Benzaldehydes
  • Esters
  • Ethylamines
  • Fluorine
  • triethylamine