Simple Chiral Derivatization Protocols for 1H NMR and 19F NMR Spectroscopic Analysis of the Enantiopurity of Chiral Diols

Sonia Lozano Yeste, Magdalena E Powell, Steven D Bull, Tony D James

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

Two practically simple chiral derivatization protocols for determining the enantiopurity of chiral diols by 1H NMR and 19F NMR spectroscopic analysis are described, involving treatment of the diol with 2-formylphenylboronic acid and α-methyl-4-fluorobenzylamine, or its derivatization with 4-fluoro-2-formylphenylboronic acid and α-methyl-benzylamine. Both approaches afford mixtures of imino−boronate esters whose diastereomeric ratio may be measured by 1H NMR or 19F NMR spectroscopy, the value of which is an accurate reflection of the enantiopurity of the parent diol.
Original languageEnglish
Pages (from-to)427-430
Number of pages4
JournalThe Journal of Organic Chemistry
Volume74
Issue number1
Early online date2 Dec 2008
DOIs
Publication statusPublished - 2009

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