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

Department of Chemistry

University of Bath

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

13 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

Bibliographical note

Funding Information:
This work was supported by the EPSRC Centre for Doctoral Training in Catalysis (EP/L016443/1).

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Funding

This work was supported by the EPSRC Centre for Doctoral Training in Catalysis (EP/L016443/1).

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.9b02473Licence: CC BY

Cite this

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

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.\}",

note = "Funding Information: This work was supported by the EPSRC Centre for Doctoral Training in Catalysis (EP/L016443/1). Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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AU - Chapman, Robert S.L.

AU - Ley-Smith, Harry

AU - Liu, Liyuan

AU - James, Tony D.

AU - Bull, Steven D.

PY - 2020/1/17

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N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

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ER -

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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Cite this

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

Abstract

Bibliographical note

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Equipment

Electrospray Time-of-Flight Mass Spectrometer (Open-Access)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Cite this

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