Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding

Org Lett. 2004 Jul 22;6(15):2591-3. doi: 10.1021/ol049084x.

Abstract

[structure: see text] A chiral aldehyde that forms resonance-assisted hydrogen bonded imines with amino acids has been developed. This hydrogen bond not only increases the equilibrium constant for imine formation but also provides a highly downfield-shifted NMR singlet for evaluating enantiomeric excess and absolute stereochemistry of amino acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Amino Acids / chemistry*
  • Hydrogen Bonding
  • Imines / chemistry
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Amino Acids
  • Imines
  • Indicators and Reagents