American Chemical Society
ol7b02198_si_001.pdf (7.54 MB)

Chloride-Templated Macrocyclization and Anion-Binding Properties of C2‑Symmetric Macrocyclic Ureas from Sucrose

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journal contribution
posted on 2017-08-21, 19:21 authored by Katarzyna Łęczycka-Wilk, Kajetan Dąbrowa, Piotr Cmoch, Sławomir Jarosz
A high-yielding, one-pot simultaneous synthesis and full characterization of two regioisomeric C2-symmetrical macrocycles 3a and 3b from triphosgene and readily available hexa-O-benzyl-6,6'-diaminosucrose 1 is reported. The efficient macrocyclization (90% overall yield, ∼1:1 ratio of 3a vs 3b) is attributed to favorable steric constraints and to a templation by a chloride anion. 1H NMR titration studies and theoretical predictions revealed that both receptors show similar affinity for acetate and benzoate anions and enhanced preference for chloride over H2PO4.