Simple chiral derivatization protocols for 1H NMR and 19F NMR spectroscopic analysis of the enantiopurity of chiral diols.
Two practically simple chiral derivatization protocols for determining the enantiopurity of chiral diols by (1)H NMR and (19)F NMR spectroscopic analysis are described, involving treatment of the diol with 2-formylphenylboronic acid and alpha-methyl-4-fluorobenzylamine, or its derivatization with 4-fluoro-2-formylphenylboronic acid and alpha-methyl-benzylamine. Both approaches afford mixtures of imino-boronate esters whose diastereomeric ratio may be measured by (1)H NMR or (19)F NMR spectroscopy, the value of which is an accurate reflection of the enantiopurity of the parent diol.
Yeste
Sonia Lozano
SL
Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom.
Powell
Magdalena E
ME
Bull
Steven D
SD
James
Tony D
TD
D000438:Alcohols / Q000032:analysis*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D008968:Molecular Conformation; D011522:Protons; D012015:Reference Standards; D013237:Stereoisomerism
D000438:Alcohols; D001897:Boronic Acids; D004952:Esters; D007097:Imines; D011522:Protons; D005461:Fluorine