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Synthesis of an inherently chiral O,O′-bridged thiacalix[4]crowncarboxylic acid and its application to a chiral solvating agent |
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| Authors: | Fumitaka Narumi Tetsutaro Hattori Nobuji Matsumura Hiroshi Katagiri Hiroshi Kameyama |
| Institution: | a Department of Basic Sciences, School of Science and Engineering, Ishinomaki Senshu University, 1 Shinmito, Minamisakai, Ishinomaki 986-8580, Japan b Department of Environmental Studies, Graduate School of Environmental Studies, Tohoku University, Aramaki-Aoba 07, Aoba-ku, Sendai 980-8579, Japan c Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki-Aoba, Aoba-ku, Sendai 980-8578, Japan |
| Abstract: | Treatment of readily available O,O′-1,1,3,3-tetraisopropyldisiloxane-1,3-diyl-bridged p-tert-butylthiacalix4]arene (1) with tri(ethylene glycol) di-p-tosylate and subsequent desilylation gave O,O′-bridged thiacalix4]crown 3 in an excellent yield. Mono-O-alkylation of 3 with ethyl bromoacetate, followed by optical resolution by chiral HPLC, and subsequent hydrolysis of the ester moiety gave inherently chiral O,O′-bridged thiacalix4]crowncarboxylic acid (+)-6, which clearly discriminated enantiomeric primary amines, as well as amino esters, by 1H NMR spectroscopy. |
| Keywords: | Calixarene Calixcrown Inherently chiral Chiral recognition |
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