Determination of the absolute stereochemistry and the activation barriers of thermally interconvertible heterocyclic compounds bearing a naphthyl substituent |
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| Institution: | 1. College of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, Shanxi 030006, PR China;2. China Research Institute of Daily Chemical Industry, Taiyuan, Shanxi 030001, PR China;1. Koc University, Molecular Biology and Genetics, Rumelifeneri Yolu, Istanbul, 34450, Turkey;2. Koc University, Chemical and Biological Engineering, Rumelifeneri Yolu, Istanbul, 34450, Turkey;3. Current address: Istanbul University, Faculty of Sciences, Department of Biology, Biotechnology Division, Istanbul, 34134, Turkey |
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| Abstract: | The enantiotopic methyl signals of the compounds studied were resolved in the presence of the optically active chiral auxiliary (S)-(+)-2,2,2-trifluoroanthryl ethanol, (S)-TFAE] via complex formation between (S)-TFAE and the respective compounds. Two different solvation models were proposed for both M and P conformations leading to the assignments of the 1H NMR signals and thus absolute conformations. The solvation models proposed also explained the strong temperature dependence of the 1H NMR signals upon cooling. The activation barriers for interconversion between the enantiomers of the compounds studied have been determined by either temperature dependent NMR or enantioresolution on a chiral sorbent via HPLC. |
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