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

0535708 - ÚCHP 2021 RIV DE eng J - Journal Article
Horáčková, T. - Budka, J. - Eigner, V. - Chung, W.-S. - Cuřínová, Petra - Lhoták, P.
Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation.
Beilstein Journal of Organic Chemistry. Roč. 16, DEC 7 (2020), s. 2999-3007. ISSN 1860-5397. E-ISSN 1860-5397
R&D Projects: GA ČR(CZ) GA20-07833S
Institutional support: RVO:67985858
Keywords : anion recognition * calixarene * chiral receptor
OECD category: Organic chemistry
Impact factor: 2.883, year: 2020
Method of publishing: Open access
https://www.beilstein-journals.org/s/zhaeT9EkPh

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-ʟ-phenylalaninate. The structures of some receptors were confirmed by single crystal X-ray analysis.
Permanent Link: http://hdl.handle.net/11104/0314543