Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent

Cora D. Chisholm, F. Fülöp, E. Forró, Thomas J. Wenzel

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

(18-Crown-6)-2,3,11,12-tetracarboxylic acid is an excellent chiral NMR solvating agent for cyclic β-amino acids with cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, bicyclo[2.2.1]heptane, and bicyclo[2.2.1]heptene rings. The crown ether was added to the neutral β-amino acids in methanol-d4. A neutralization reaction between the crown ether and β-amino acid forms the ammonium ion needed for favorable association. Enantiomeric discrimination of the two hydrogen atoms α to the amine and carboxylic acid moieties of the β-amino acid was observed with every substrate studied. Trends in the order of the enantiomeric discrimination of certain hydrogen atoms for substrates of similar structures correlate with the absolute configuration.

Original languageEnglish
Pages (from-to)2289-2294
Number of pages6
JournalTetrahedron Asymmetry
Volume21
Issue number18
DOIs
Publication statusPublished - Sep 27 2010

Fingerprint

Cyclic Amino Acids
Crown Ethers
Cyclopentanes
Cycloheptanes
amino acids
discrimination
Amino acids
Hydrogen
Nuclear magnetic resonance
Neutral Amino Acids
Amino Acids
Crown ethers
Atoms
nuclear magnetic resonance
acids
Acids
Substrates
Carboxylic Acids
Ammonium Compounds
Amines

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent. / Chisholm, Cora D.; Fülöp, F.; Forró, E.; Wenzel, Thomas J.

In: Tetrahedron Asymmetry, Vol. 21, No. 18, 27.09.2010, p. 2289-2294.

Research output: Contribution to journalArticle

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