Structurally simple chiral thioureas as chiral solvating agents in the enantiodiscrimination of α-hydroxy and α-amino carboxylic acids

Hernández‐Rodríguez, Marcos; Juaristi, Eusebio

doi:10.1016/j.tet.2007.05.021

Cited by 48 publications

(26 citation statements)

References 87 publications

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“…PETU was prepared from simple reaction of enantiopure α‐phenylethyl amine with enantiopure α‐phenylethyl isothiocyanate in pentane. The identity was confirmed by comparison with literature data …”

Section: Methodssupporting

confidence: 57%

“…The identity was confirmed by comparison with literature data. [21] IR and VCD spectroscopy Spectra were recorded on aB ruker Vertex 70 Vs pectrometer equipped with aP MA 50 module for polarization modulated measurements. Solutions were held in as ealed transmission cell with BaF 2 windows and either 100 or 200 mmp ath length.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

See 1 more Smart Citation

Towards an Observation of Active Conformations in Asymmetric Catalysis: Interaction‐Induced Conformational Preferences of a Chiral Thiourea Model Compound

Kreienborg

Pollok

Merten

2016

Chemistry A European J

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The observation of the active species is the goal of most spectroscopic investigations on enantioselective organocatalysts in solution. Although NMR spectroscopy is widely applied, it has low sensitivity for conformational changes or the chiral nature of the interactions. In the present work, we exemplify the use of vibrational circular dichroism (VCD) spectroscopy for the characterization of a chiral thiourea model compound in nonpolar and polar solvents, as well as for a detailed analysis of its interaction with a model reactant. We discuss solvent-induced conformational changes of the thiourea, and provide evidence for an unexpected binding topology between the thiourea and an acetate anion. The results clearly showcase the possibilities offered by using VCD spectroscopy in the characterization of chiral organocatalysts.

show abstract

Section: Methodssupporting

confidence: 57%

Section: Experimental Section Materialsmentioning

confidence: 99%

Towards an Observation of Active Conformations in Asymmetric Catalysis: Interaction‐Induced Conformational Preferences of a Chiral Thiourea Model Compound

Kreienborg

Pollok

Merten

2016

Chemistry A European J

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show abstract

“…Fluorescent sensors that can differentiate the two enantiomers of a chiral compound should provide a real time technique for rapid chiral assays with many unique advantages compared with the ESI-MS spectra, NMR, UV-Vis and electrophoresis [207][208][209][210]. The chiral recognition of AAs and peptides is a fundamental process for regulating various functions in living systems, particularly in connection with the application of high throughput combinatorial techniques [211].…”

Section: Chiral/enantiomeric Recognitionmentioning

confidence: 99%

Fluorescent/luminescent detection of natural amino acids by organometallic systems

Wang

Liu

Tong

et al. 2015

Coordination Chemistry Reviews

120

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“…tert-Butyl azide, [16] neopentylamine, [27] and N,N'-dineopentyl-and N,N'-dicyclohexylthioureas [28] were obtained according to the literature procedures.…”

Section: Bfmentioning

confidence: 99%

New Lipophilic 2‐Amino‐N,N′‐dialkyl‐4,5‐dimethylimidazolium Cations: Synthesis, Structure, Properties, and Outstanding Thermal Stability in Alkaline Media

Kunetskiy

Cı́sařová

Šaman

et al. 2009

Chemistry A European J

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A series of new N,N'-dialkyl-4,5-dimethylimidazolium cations possessing electron-rich 2-imidazolylidene- or phosphoranylidene-amino substituents has been efficiently synthesized from common precursors, N,N'-dialkyl-4,5-dimethylimidazol-2-ylidenes. The new lipophilic salts obtained have been found to be highly stable towards strong alkali under both biphasic and homogeneous conditions. Their exceptional aqueous base resistance, which has hitherto only been seen with peralkylated polyaminophosphazenium cations, may be attributed to three factors: aromatic stabilization, efficient resonance charge delocalization, and steric protection of the exocyclic nitrogen linkage due to bulky lipophilic N-alkyl substituents.

show abstract

Structurally simple chiral thioureas as chiral solvating agents in the enantiodiscrimination of α-hydroxy and α-amino carboxylic acids

Cited by 48 publications

References 87 publications

Towards an Observation of Active Conformations in Asymmetric Catalysis: Interaction‐Induced Conformational Preferences of a Chiral Thiourea Model Compound

Towards an Observation of Active Conformations in Asymmetric Catalysis: Interaction‐Induced Conformational Preferences of a Chiral Thiourea Model Compound

Fluorescent/luminescent detection of natural amino acids by organometallic systems

New Lipophilic 2‐Amino‐N,N′‐dialkyl‐4,5‐dimethylimidazolium Cations: Synthesis, Structure, Properties, and Outstanding Thermal Stability in Alkaline Media

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