Simple protocols for NMR analysis of the enantiomeric purity of chiral diols.
A three-component chiral derivatization protocol for determining the enantiopurity of chiral diols by (1)H NMR spectroscopic analysis is described here. The present approach involves the derivatization of 1,2- 1,3- and 1,4-diols with 2-formylphenylboronic acid and enantiopure alpha-methylbenzylamine. This method affords a mixture of diastereoisomeric iminoboronate esters whose ratio can be determined by integration of well-resolved diastereotopic resonances in their (1)H NMR spectra, thus enabling the determination of the enantiopurity of the parent diol. The protocol as described takes less than 90 min to complete.
Kelly
Andrew M
AM
Department of Chemistry, University of Bath, Bath BA2 7AY, UK.
Pérez-Fuertes
Yolanda
Y
Fossey
John S
JS
Yeste
Sonia Lozano
SL
Bull
Steven D
SD
James
Tony D
TD
D000438:Alcohols / Q000737:chemistry* / Q000378:metabolism; D001547:Benzaldehydes / Q000737:chemistry; D001596:Benzylamines / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry; D013237:Stereoisomerism
C532809:2-formylphenylboronic acid; D000438:Alcohols; D001547:Benzaldehydes; D001596:Benzylamines; D001897:Boronic Acids; D004952:Esters; D010627:Phenethylamines; C033198:1-phenethylamine