Chiral Anion Recognition by a Ureido-Thiacalix[4]arene Ligand Immobilized in the 1,3-Alternate Conformation

0440911 - ÚCHP 2016 RIV GB eng J - Journal Article
Mačková, M. - Mikšátko, J. - Budka, J. - Eigner, V. - Cuřínová, Petra - Lhoták, P.
Chiral Anion Recognition by a Ureido-Thiacalix[4]arene Ligand Immobilized in the 1,3-Alternate Conformation.
New Journal of Chemistry. Roč. 39, č. 2 (2015), s. 1382-1389. ISSN 1144-0546. E-ISSN 1369-9261
Grant - others:GA ČR(CZ) GAP207/12/2027
Institutional support: RVO:67985858
Keywords : uncommon regioselectivity * receptors * thiacalixarenes
Subject RIV: CC - Organic Chemistry
Impact factor: 3.277, year: 2015

While all the alkylation methods commonly used in the chemistry of classical calixarenes failed, tetranitrothiacalix[4]arene was easily alkylated using various alcohols under Mitsunobu reaction conditions. The products thus obtained were immobilized in the 1,3-alternate conformation as suggested by 1H NMR and proven unequivocally by X-ray analysis. The introduction of chiral alkyl substituents into the lower rim of thiacalixarene gave us an opportunity to form well-preorganized ureido cavities on both sites of the system. As revealed by 1H NMR titration experiments, such compounds were capable of chiral anion recognition even in DMSO-d6 which is a highly competitive solvent towards hydrogen bonding interactions. The highest chiral discrimination was achieved for free serine with a selectivity factor of 3.13 for the D-isomer.
Permanent Link: http://hdl.handle.net/11104/0245460