The glycoluril monomer is a popular building block in supramolecular chemistry as it is used for the synthesis of versatile host molecules which can interact with cationic, anionic or neutral guest molecules. Here we present the design and synthesis of a new hybrid macrocycle containing glycoluril and aromatic units. The reaction afforded a mixture of macrocyclic homologues from which a two-membered macrocycle was isolated as the main product. Two disastereomers of the macrocycle were separated and characterized by means of NMR spectroscopy and X-ray crystallography. Conformational changes of these diastereomers were investigated using DFT models and variable-temperature NMR.

Department of Chemistry and RECETOX Masaryk University Kamenice 5 625 00 Brno Czech Republic

Zobrazit více v PubMed

Sessler J L, Gale P A, Cho W-S. Anion Receptor Chemistry. Cambridge, U.K.: Royal Society of Chemistry; 2006. ((Monographs in Supramolecular Chemistry)).

Gale P A, Howe E N W, Wu X. Chem. 2016;1:351–422. doi: 10.1016/j.chempr.2016.08.004. DOI

Langton M J, Serpell C J, Beer P D. Angew Chem, Int Ed. 2016;55:1974–1987. doi: 10.1002/anie.201506589. PubMed DOI PMC

Blažek Bregović V, Basarić N, Mlinarić-Majerski K. Coord Chem Rev. 2015;295:80–124. doi: 10.1016/j.ccr.2015.03.011. DOI

Shimizu L S, Smith M D, Hughes A D, Shimizu K D. Chem Commun. 2001;(17):1592–1593. doi: 10.1039/b102159c. PubMed DOI

Wu Z, Hu T, He L, Gong B. Org Lett. 2012;14:2504–2507. doi: 10.1021/ol300684j. PubMed DOI

Xing L, Ziener U, Sutherland T C, Cuccia L A. Chem Commun. 2005;(46):5751–5753. doi: 10.1039/b510118b. PubMed DOI

Prusinowska N, Szymkowiak J, Kwit M. J Org Chem. 2018;83:1167–1175. doi: 10.1021/acs.joc.7b02600. PubMed DOI

Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L. Angew Chem, Int Ed. 2005;44:4844–4870. doi: 10.1002/anie.200460675. PubMed DOI

Andersen N N, Lisbjerg M, Eriksen K, Pittelkow M. Isr J Chem. 2018;58:435–448. doi: 10.1002/ijch.201700129. DOI

Svec J, Necas M, Sindelar V. Angew Chem, Int Ed. 2010;49:2378–2381. doi: 10.1002/anie.201000420. PubMed DOI

Lizal T, Sindelar V. Isr J Chem. 2018;58:326–333. doi: 10.1002/ijch.201700111. DOI

Yawer M A, Havel V, Sindelar V. Angew Chem, Int Ed. 2015;54(1):276–279. doi: 10.1002/anie.201409895. PubMed DOI

Fiala T, Sleziakova K, Marsalek K, Salvadori K, Sindelar V. J Org Chem. 2018;83:1903–1912. doi: 10.1021/acs.joc.7b02846. PubMed DOI

Havel V, Yawer M A, Sindelar V. Chem Commun. 2015;51:4666–4669. doi: 10.1039/c4cc10108a. PubMed DOI

Roy K, Wang C, Smith M D, Pellechia P J, Shimizu L S. J Org Chem. 2010;75:5453–5460. doi: 10.1021/jo1009596. PubMed DOI

Sindt A J, Smith M D, Pellechia P J, Shimizu L S. Cryst Growth Des. 2018;18:1605–1612. doi: 10.1021/acs.cgd.7b01558. DOI

Havel V, Svec J, Wimmerova M, Dusek M, Pojarova M, Sindelar V. Org Lett. 2011;13:4000–4003. doi: 10.1021/ol201515c. PubMed DOI

Fulmer G R, Miller A J M, Sherden N H, Gottlieb H E, Nudelman A, Stoltz B M, Bercaw J E, Goldberg K I. Organometallics. 2010;29:2176–2179. doi: 10.1021/om100106e. DOI