Functionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates
Status PubMed-not-MEDLINE Language English Country Germany Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- anion receptors, enantioselective recognition, glycolurils, host-guest systems, macrocycles,
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non-functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host-guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals. Their supramolecular properties in terms of carboxylate binding were studied by means of NMR in DMSO-d6 . The reported bambusurils bind selected chiral carboxylates with enantioselectivity factors up to 3.1. The results indicated that the selectivity towards different carboxylates is governed by the steric constraint of the substituents surrounding bambusuril portals. No clear trend in the binding affinities and their enantioselectivities was found.
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Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils
