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 › peer-review

2 Citations (SciVal)

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
Number of pages	8
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

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10.1021/acs.joc.9b02473Licence: CC BY

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A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by ¹H and ¹⁹F NMR Spectroscopy. / Groleau, Robin R.; Chapman, Robert S.L.; Ley-Smith, Harry; Liu, Liyuan; James, Tony D.; Bull, Steven D.

In: Journal of Organic Chemistry, Vol. 85, No. 2, 17.01.2020, p. 1208-1215.

Research output: Contribution to journal › Article › peer-review

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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.",

author = "Groleau, {Robin R.} and Chapman, {Robert S.L.} and Harry Ley-Smith and Liyuan Liu and James, {Tony D.} and Bull, {Steven D.}",

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

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