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 | |
| Publication status | Published - 17 Jan 2020 |
ASJC Scopus subject areas
- Organic Chemistry
Cite this
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
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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 -