Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation

Tereza HoráčkovÃi, Jan Budka, Vaclav Eigner, Wen Sheng Chung, Petra CuÅínovÃi, Pavel Lhoták*

*Corresponding author for this work

研究成果: Article同行評審

摘要

The introduction of chiral alkyl substituents into the lower rim of calix[4]arene immobilised in the 1,3-alternate conformation led to a system possessing a preorganised ureido cavity hemmed with chiral alkyl units in the near proximity. As shown by the 1H NMR titration experiments, these compounds can be used as receptors for chiral anions in DMSO-d6. The chiral recognition ability can be further strengthened by the introduction of another chiral moiety directly onto the urea N atoms. The systems with double chiral units being located around the binding ureido cavity showed better stereodiscrimination, with the highest selectivity factor being 3.33 (KL/KD) achieved for N-acetyl-Ê -phenylalaninate. The structures of some receptors were confirmed by single crystal X-ray analysis.

原文English
頁(從 - 到)2999-3007
頁數9
期刊Beilstein Journal of Organic Chemistry
16
DOIs
出版狀態Published - 7 十二月 2020

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