Synthesis of Chiral Crownophanes Having Two Phenolic Groups via Tandem Claisen Rearrangement and Their Chiral Recognition |
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Authors: | Hideo Tokuhisa Tamako Ogihara Yoshinobu Nagawa Kazuhisa Hiratani |
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Institution: | (1) National Institute for Advanced Interdisciplinary Research, 1-1-4 Higashi, Tsukuba, Ibaraki, 305-8562, Japan |
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Abstract: | Asymmetric crownophanes having a chiral binaphthyl unit and two phenolic hydroxyl groups were thermally synthesized from the corresponding macrocyclic ethers via tandem Claisen rearrangement. Circular dichroism (CD) spectroscopic studies and HPLC experiments confirmed that little racemization of these crownophanes occurred during the thermal rearrangement. The association constants for the interaction of the chiral crownophanes with the enantiomers of phenylethylamine, phenylglycinol, and phenylalaninol were determined by a 1H NMR titration method in CD2Cl2. As a result, the 27 membered crownophane has some chiral recognition for phenylglycinol. |
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Keywords: | binaphthyl chiral crownophanes Claisen rearrangement chiral recognition |
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