Related Experiment Video
Updated: May 24, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Chiral discrimination of aliphatic amines and amino alcohols using NMR spectroscopy
Thomas J Wenzel1, Ryan D Rollo, Rebecca L Clark
1Department of Chemistry, Bates College, Lewiston, ME 04240, USA. twenzel@bates.edu
Abstract:
Two methods are compared for analyzing the enantiomeric purity of aliphatic amines and amino alcohols using NMR spectroscopy. The first employs (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent in methanol-d(4) . The second involves a derivatization scheme in which the amine is reacted with naphtho[2,3-c]furan-1,3-dione to form the corresponding amide. The naphthyl amide is then mixed with a chiral calix[4]resorcinarene in deuterium oxide. The crown ether only produces sufficient enantiomeric discrimination to determine enantiomeric purity for three of the nine substrates studied. The system with the naphthyl amide and a calix[4]resorcinarene produces enantiomeric discrimination of sufficient magnitude to determine enantiomeric purity for all nine substrates. The H1 and H4 resonances of the naphthyl ring are especially suitable to monitor for enantiomeric discrimination. The order of the (R)- and (S)-enantiomers of the H1 and H4 resonances exhibit specific trends for aliphatic amines and amino alcohols that correlate with the absolute configuration.
More Related Videos
Related Concept Videos
NMR Spectroscopy Of Amines
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Structure of Amines
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
NMR Spectroscopy and Mass Spectrometry of Aldehydes and Ketones
Mass Spectrometry of Amines

