Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 1, Pages 427-430Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo8019187
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Two practically simple chiral derivatization protocols for determining the enantiopurity of chiral diols by H-1 NMR and F-19 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-benzyl-amine. Both approaches afford mixtures of imino-boronate esters whose diastereomeric ratio may be measured by H-1 NMR or F-19 NMR spectroscopy, the value of which is an accurate reflection of the enantiopurity of the parent diol.
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