Chiral Host-Guest Interaction. A Water-Soluble Calix[4]resorcarene Having L-Proline Moieties as a Non-Lanthanide Chiral NMR Shift Reagent for Chiral Aromatic Guests in Water

Yanagihara, Ryoji; Tominaga, Makio; Aoyama, Yasuhiro

doi:10.1021/jo00101a061

Cited by 74 publications

(44 citation statements)

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“…Only one set of substrate resonances are observed and the chemical shifts are identical to those of the ammonium ion without any calix [4]resorcarene. Despite a literature report in which an L-proline derivative of a sulfated calix [4]resorcarene was found to be a useful chiral NMR solvating agent in water, 16 the amine derivatives we prepared do not appear to have practical applications as chiral NMR solvating agents in chloroform.…”

Section: S154mentioning

confidence: 74%

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Calix[4]arene, calix[4]resorcarene, and cyclodextrin derivatives and their lanthanide complexes as chiral NMR shift reagents

et al. 2003

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Calix[4]arenes, calix[4]resorcarenes, and anionic cyclodextrin derivatives were examined as chiral NMR solvating agents. The calix[4]arenes were prepared by attachment of amino acids through the hydroxyl groups of the phenol rings. Chloroform-, methanol-, and water-soluble derivatives were prepared and tested with a range of substrates. Chloroform-soluble chiral calix[4]resorcarenes were prepared by attachment of chiral primary and secondary amines and examined in NMR applications with a variety of substrates. Sulfated and carboxymethylated beta-cyclodextrin are effective at causing enantiomeric discrimination in the (1)H NMR spectra of organic cations. Lanthanide ions associate at the carboxymethyl groups and cause sizeable shifts and enhancements in enantiomeric discrimination in the spectra of organic cations. The enhancements caused by the lanthanide ion are large enough that much lower concentrations of the cyclodextrin can be used as compared to conventional analyses.

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Section: S154mentioning

confidence: 74%

“…[16][17][18] Calixarenes are formed by a condensation reaction of formaldehyde and substituted phenols. Specific variations of the reaction conditions lead to basket-shaped compounds with four or more phenol rings.…”

mentioning

confidence: 99%

Calix[4]arene, calix[4]resorcarene, and cyclodextrin derivatives and their lanthanide complexes as chiral NMR shift reagents

et al. 2003

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“…52,55 Substrates were purchased as hydrochloride salts when available. For those substrates only available in neutral form, hydrochloride salts were obtained in solution by adding a stoichiometric equivalent of hydrochloric acid in deuterium oxide.…”

Section: Materials and Methods Reagentsmentioning

confidence: 99%

“…This compound is an effective chiral NMR solvating agent for water-soluble substrates with a phenyl or bicyclic aromatic ring. [52][53][54][55][56] Compounds similar to 1 that contain optically pure hydroxyprolinylmethyl substituents including cis-4-hydroxy-L-proline (2), trans-4-hydroxy-Lproline (3), and trans-3-hydroxy-L-proline (4) have since been studied and often function more effectively as chiral NMR solvating agents than 1 for phenyl-containing compounds. 55,56 Compounds 1-4 adopt a cone configuration in solution or are in rapid exchange among a variety of possible configurations (see Fig.…”

Section: Introductionmentioning

confidence: 99%

Water‐soluble calix[4]resorcinarenes as chiral NMR solvating agents for bicyclic aromatic compounds

2009

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Water-soluble calix[4]resorcinarenes with proline, 3-hydroxyproline, and 4-hydroxyproline substituent groups are evaluated as chiral NMR solvating agents on a series of bicyclic aromatic compounds with naphthyl, indole, dihydroindole, and indane rings. The substrates interact with the calixresorcinarene through insertion of the aromatic ring into the cavity. Most of the substrates are analyzed as cationic species, although one anionic species is analyzed. All of the substrates exhibit enantiomeric discrimination in the 1H-NMR spectrum with one or more of the calixresorcinarenes. In most cases, the hydroxyproline derivatives are more effective at causing enantiodifferentiation than the corresponding proline derivative. Presumably, the hydroxyl group on the proline moieties is involved in interactions with the substituent groups of the substrate that are important in creating chiral recognition. The enantiomeric discrimination in the 1H-NMR spectrum is large enough for many resonances to permit the analysis of enantiomeric purity.

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“…[25][26][27] SCR-Pro exists in aqueous solution in a cone-shaped configuration with a well-defined cavity. Water-soluble organic salts with mono-or ortho-substituted phenyl rings and mono-or 2,3-disubstituted naphthyl rings form host-guest complexes by insertion of the aromatic ring into the cavity of SCR-Pro.…”

Section: Introductionmentioning

confidence: 99%

Water‐Soluble Calix[4]resorcinarenes with Hydroxyproline Groups as Chiral NMR Solvating Agents for Phenyl‐ and Pyridyl‐Containing Compounds

Hagan¹,

O'Farrell²,

Wenzel³

2009

Eur J Org Chem

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A series of water‐soluble sulfonated calix[4]resorcinarenes with L‐proline, cis‐4‐hydroxy‐d‐ and ‐L‐proline, trans‐4‐hydroxy‐L‐proline and trans‐3‐hydroxy‐L‐proline are evaluated as chiral NMR solvating agents. The changes in chemical shifts and enantiomeric discrimination in the 1H NMR spectra of a variety of phenyl‐ and pyridyl‐containing compounds are reported. Substrates associate by insertion of the phenyl or pyridyl ring into the cavity of the calix[4]resorcinarene. Series of compounds with methylbenzylamine and benzyl alcohol units are among those examined. For many compounds, the calix[4]resorcinarenes with the hydroxyproline groups are more effective chiral NMR solvating agents than the corresponding proline derivative. The trans‐4‐ and trans‐3‐hydroxy‐L‐proline derivatives are especially effective as chiral NMR solvating agents. Enantiomeric discrimination in the 1H NMR spectra is often large enough to facilitate the analysis of enantiomeric purity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Chiral Host-Guest Interaction. A Water-Soluble Calix[4]resorcarene Having L-Proline Moieties as a Non-Lanthanide Chiral NMR Shift Reagent for Chiral Aromatic Guests in Water

Cited by 74 publications

References 0 publications

Calix[4]arene, calix[4]resorcarene, and cyclodextrin derivatives and their lanthanide complexes as chiral NMR shift reagents

Calix[4]arene, calix[4]resorcarene, and cyclodextrin derivatives and their lanthanide complexes as chiral NMR shift reagents

Water‐soluble calix[4]resorcinarenes as chiral NMR solvating agents for bicyclic aromatic compounds

Water‐Soluble Calix[4]resorcinarenes with Hydroxyproline Groups as Chiral NMR Solvating Agents for Phenyl‐ and Pyridyl‐Containing Compounds

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