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

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)2999-3007
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume16
DOIs
StatePublished - 7 Dec 2020

Keywords

  • Anion recognition
  • Calixarene
  • Chiral receptor
  • Complexation
  • Enantiodiscrimination

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