Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils

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Authors	SLÁVIK Petr TORRISI Jacopo JURČEK Pia Yasmine SOKOLOV Jan ŠINDELÁŘ Vladimír
Year of publication	2023
Type	Article in Periodical
Magazine / Source	Journal of Organic Chemistry
MU Faculty or unit	Faculty of Science
Citation
Web	https://pubs.acs.org/doi/10.1021/acs.joc.3c00667
Doi	http://dx.doi.org/10.1021/acs.joc.3c00667
Keywords	FLUORINATED BAMBUSURILS; DEPROTECTION; RECOGNITION; CUCURBITURIL; CATALYSTS; BINDING; WATER; ALKYL
Attached files	2309497.pdf
Description	A general strategyfor the synthesis of 2N,4N & PRIME;-disubstitutedglycoluril enantiomers on a multigramscale using orthogonal protection is reported. The use of these glycolurilsis demonstrated in the synthesis of enantiomerically pure bambus[6]urilmacrocycles. Moreover, the deprotection of (S)-1-phenylethylsubstituents on the macrocycle was achieved, opening access to variouschiral bambus[6]urils via post-macrocyclization modificationstrategy.
Related projects:	CETOCOEN Excellence CETOCOEN Excellence Czech Infrastructure for Integrative Structural Biology RECETOX RI Molecules, complexes, macrocycles, and xerogels Chemical modification of bambusurils for adjusting their binding affinity and selectivity