Organic Letters
Organic Letters
5 years ago

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

Chloride-Templated Macrocyclization and Anion-Binding Properties of C2-Symmetric Macrocyclic Ureas from Sucrose
Piotr Cmoch, Kajetan Dąbrowa, Katarzyna Łęczycka-Wilk, 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–.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02198

DOI: 10.1021/acs.orglett.7b02198

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