新型手性杯[4]芳烃的合成与表征。

Enantiomer Pub Date : 2002-03-01 DOI:10.1080/10242430212191
Y. Okada, M. Mizutani, Fuyuhiko Ishii, J. Nishimura*
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引用次数: 7

摘要

采用Williamson醚合成和温和Lewis酸逐级醚裂解两种方法成功合成了独特的手性杯芳烃。后一种方法具有较高的区域选择性。以低聚乙二醇为单元的离子载体对K+、Rb+、Cs+等较大碱金属离子的萃取效率高于Li+、Na+等较小碱金属离子。它们的离子选择性明显受冠醚链长的影响。所得的所有外消旋物均可通过手性柱的高效液相色谱拆分为各对映体。具有平面手性的杯芳烃能够识别客体分子的手性。因此,(-)受体与(R)-(+)- -苯基乙基苦味酸铵强烈地形成1:1的配合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis and characterization of new chiral calix[4]arenes.
The unique chiral calixarenes were successfully synthesized by the following two methods: the Williamson ether synthesis and a stepwise ether cleavage with a mild Lewis acid. The high regioselectivity is recognized by the latter stepwise method. The ionophores having oligoethylene glycol unit efficiently extracted larger alkali metal ions like K+, Rb+, and Cs+ than smaller ones like Li+ and Na+. Their ion selectivity apparently changed by the chain length of crown ether. All racemates obtained could be resolved to each enantiomer by HPLC using a chiral column. The calixarenes with planar chirality recognized the chirality of guest molecules. Thus, the (-)-receptor resolved strongly forms 1:1 complex with (R)-(+)-alpha-phenylethylammonium picrate.
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