On the Racemization of Chiral Imidazolines
| Autor: | Teresa Bartholomeyzik, Heewon Lee, Carl A. Busacca, Sreedhar Cheekoori, Sherry Shen, Anjan Saha, Shengli Ma, Nelu Grinberg, Chris H. Senanayake |
|---|---|
| Rok vydání: | 2008 |
| Předmět: |
chemistry.chemical_classification
Magnetic Resonance Spectroscopy Base (chemistry) Stereochemistry Organic Chemistry Imidazoles Molecular Conformation Imidazoline receptor Stereoisomerism Ligands Ring (chemistry) Medicinal chemistry Mass Spectrometry Unexpected finding Isomerism chemistry Solvents Dimethyl Sulfoxide Amine gas treating Chromatography Thin Layer Conrotatory and disrotatory Racemization Chromatography High Pressure Liquid |
| Zdroj: | The Journal of Organic Chemistry. 73:9756-9761 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Racemization of chiral imidazolines with base has been studied for the first time following an unexpected finding in the synthesis of chiral imidazoline ligands. Amine bases do not cause racemization. Strong inorganic bases can induce racemization, yet this occurs only when the nitrogen is unsubstituted, in agreement with a symmetry-allowed thermal disrotatory ring opening and closure from a diazapentadienyl anion. Surprisingly, even with electron-withdrawing N-substituents, no racemization is observed. Conditions which allow for the racemization-free manipulations of this important compound class have been defined and developed. |
| Databáze: | OpenAIRE |
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