Azacalix[4]arene tetramethyl ether with inherent chirality generated by substitution on the nitrogen bridges |
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Authors: | Koichi Ishibashi Hirohito Tsue Hiroki Takahashi Rui Tamura |
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Affiliation: | Graduate School of Human and Environmental Studies, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan |
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Abstract: | The first inherently chiral azacalix[4]arene has been prepared by introducing three benzyl groups onto the nitrogen bridges. The highly enantioenriched compound was easily obtained via a moderately enantioselective cyclization followed by a simple crystallization procedure. NMR and X-ray crystallographic studies revealed that easy access to the enantiomer was permitted by the non-racemizable 1,3-alternate conformation in solution, up to 110 °C, as well as by the preferential crystallization of a racemic compound. |
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