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

doi:10.1021/acs.joc.9b02473

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 journal › Article

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 language	English
Pages (from-to)	1208-1215
Journal	Journal of Organic Chemistry
Volume	85
Issue number	2
Early online date	27 Nov 2019
DOIs	https://doi.org/10.1021/acs.joc.9b02473
Publication status	Published - 17 Jan 2020

ASJC Scopus subject areas

Organic Chemistry

Cite this

Groleau, R. R., Chapman, R. S. L., Ley-Smith, H., Liu, L., James, T. D., & Bull, S. D. (2020). A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by ¹H and ¹⁹F NMR Spectroscopy. Journal of Organic Chemistry, 85(2), 1208-1215. https://doi.org/10.1021/acs.joc.9b02473

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AU - Bull, Steven D.

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