A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

Org Lett. 2013 Feb 15;15(4):860-3. doi: 10.1021/ol303566k. Epub 2013 Feb 4.

Abstract

A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by (1)H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzaldehydes / chemistry*
  • Boronic Acids / chemistry*
  • Combinatorial Chemistry Techniques
  • Esters
  • Hydroxylamines / chemistry*
  • Magnetic Resonance Spectroscopy / methods*
  • Molecular Structure
  • Naphthols / chemistry
  • Stereoisomerism

Substances

  • 2-formylphenylboronic acid
  • BINOL, naphthol
  • Benzaldehydes
  • Boronic Acids
  • Esters
  • Hydroxylamines
  • Naphthols