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

Access to Document

10.1021/acs.joc.9b02473Licence: CC BY

Link to publication in Scopus

Fingerprint Dive into the research topics of 'A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by <sup>1</sup>H and <sup>19</sup>F NMR Spectroscopy'. Together they form a unique fingerprint.

Cite this

@article{4acd8ded2fc3424db6e7199b659be10e,

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.}",

year = "2020",

month = jan,

day = "17",

doi = "10.1021/acs.joc.9b02473",

language = "English",

volume = "85",

pages = "1208--1215",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

AU - Groleau, Robin R.

AU - Chapman, Robert S.L.

AU - Ley-Smith, Harry

AU - Liu, Liyuan

AU - James, Tony D.

AU - Bull, Steven D.

PY - 2020/1/17

Y1 - 2020/1/17

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.

UR - http://www.scopus.com/inward/record.url?scp=85077113151&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b02473

DO - 10.1021/acs.joc.9b02473

M3 - Article

C2 - 31774680

AN - SCOPUS:85077113151

VL - 85

SP - 1208

EP - 1215

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -