Enantiomeric discrimination of isoxazoline fused β-amino acid derivatives using (18-Crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent

Jessica A. Howard, Melinda Nonn, F. Fülöp, Thomas J. Wenzel

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

(18-Crown-6)-2,3,11,12-tetracarboxylic acid is a useful chiral NMR solvating agent for isoxazoline-fused β-amino acid derivatives. Isoxazoline substrates are analyzed as their hydrochloride salts in methanol-d4. The crown ether and substrate associate through the formation of three hydrogen bonds between the protonated amine and crown ether oxygen atoms. Enantiomeric discrimination is observed for two or more resonances of every substrate. At least one of these resonances is free of overlap with other resonances in the spectrum and has large enough enantiomeric discrimination to enable the determination of enantiomeric purity. 2D COSY methods can be used to identify additional resonances that exhibit enantiomeric discrimination in the NMR spectrum.

Original languageEnglish
Pages (from-to)48-53
Number of pages6
JournalChirality
Volume25
Issue number1
DOIs
Publication statusPublished - Jan 2013

Fingerprint

Crown Ethers
Amino acids
Nuclear magnetic resonance
Derivatives
Amino Acids
Crown ethers
Acids
Amines
Methanol
Hydrogen
Substrates
Salts
Oxygen
Hydrogen bonds
Atoms
18-crown-6 2,3,11,12-tetracarboxylic acid

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

Enantiomeric discrimination of isoxazoline fused β-amino acid derivatives using (18-Crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent. / Howard, Jessica A.; Nonn, Melinda; Fülöp, F.; Wenzel, Thomas J.

In: Chirality, Vol. 25, No. 1, 01.2013, p. 48-53.

Research output: Contribution to journalArticle

@article{888c8f4fca3c4971bc3deb3802ac3a6c,
title = "Enantiomeric discrimination of isoxazoline fused β-amino acid derivatives using (18-Crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent",
abstract = "(18-Crown-6)-2,3,11,12-tetracarboxylic acid is a useful chiral NMR solvating agent for isoxazoline-fused β-amino acid derivatives. Isoxazoline substrates are analyzed as their hydrochloride salts in methanol-d4. The crown ether and substrate associate through the formation of three hydrogen bonds between the protonated amine and crown ether oxygen atoms. Enantiomeric discrimination is observed for two or more resonances of every substrate. At least one of these resonances is free of overlap with other resonances in the spectrum and has large enough enantiomeric discrimination to enable the determination of enantiomeric purity. 2D COSY methods can be used to identify additional resonances that exhibit enantiomeric discrimination in the NMR spectrum.",
author = "Howard, {Jessica A.} and Melinda Nonn and F. F{\"u}l{\"o}p and Wenzel, {Thomas J.}",
year = "2013",
month = "1",
doi = "10.1002/chir.22114",
language = "English",
volume = "25",
pages = "48--53",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "1",

}

TY - JOUR

T1 - Enantiomeric discrimination of isoxazoline fused β-amino acid derivatives using (18-Crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent

AU - Howard, Jessica A.

AU - Nonn, Melinda

AU - Fülöp, F.

AU - Wenzel, Thomas J.

PY - 2013/1

Y1 - 2013/1

N2 - (18-Crown-6)-2,3,11,12-tetracarboxylic acid is a useful chiral NMR solvating agent for isoxazoline-fused β-amino acid derivatives. Isoxazoline substrates are analyzed as their hydrochloride salts in methanol-d4. The crown ether and substrate associate through the formation of three hydrogen bonds between the protonated amine and crown ether oxygen atoms. Enantiomeric discrimination is observed for two or more resonances of every substrate. At least one of these resonances is free of overlap with other resonances in the spectrum and has large enough enantiomeric discrimination to enable the determination of enantiomeric purity. 2D COSY methods can be used to identify additional resonances that exhibit enantiomeric discrimination in the NMR spectrum.

AB - (18-Crown-6)-2,3,11,12-tetracarboxylic acid is a useful chiral NMR solvating agent for isoxazoline-fused β-amino acid derivatives. Isoxazoline substrates are analyzed as their hydrochloride salts in methanol-d4. The crown ether and substrate associate through the formation of three hydrogen bonds between the protonated amine and crown ether oxygen atoms. Enantiomeric discrimination is observed for two or more resonances of every substrate. At least one of these resonances is free of overlap with other resonances in the spectrum and has large enough enantiomeric discrimination to enable the determination of enantiomeric purity. 2D COSY methods can be used to identify additional resonances that exhibit enantiomeric discrimination in the NMR spectrum.

UR - http://www.scopus.com/inward/record.url?scp=84871614873&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84871614873&partnerID=8YFLogxK

U2 - 10.1002/chir.22114

DO - 10.1002/chir.22114

M3 - Article

VL - 25

SP - 48

EP - 53

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 1

ER -