A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

Robin R. Groleau, Robert S.L. Chapman, Harry Ley-Smith, Liyuan Liu, Tony D. James, Steven D. Bull

Research output: Contribution to journalArticle

Abstract

A practically simple three-component chiral derivatization protocol has been developed to determine the enantiopurity of eight S-chiral sulfinamides by 1H and 19F NMR spectroscopic analysis, based on their treatment with a 2-formylphenylboronic acid template and enantiopure pinanediol to afford a mixture of diastereomeric sulfiniminoboronate esters whose diastereomeric ratio is an accurate reflection of the enantiopurity of the parent sulfinamide.

Original languageEnglish
Pages (from-to)1208-1215
JournalJournal of Organic Chemistry
Volume85
Issue number2
Early online date27 Nov 2019
DOIs
Publication statusPublished - 17 Jan 2020

ASJC Scopus subject areas

  • Organic Chemistry

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