Chloride-Templated Macrocyclization and Anion-Binding
Properties of C2‑Symmetric Macrocyclic
Ureas from Sucrose
Posted on 2017-08-21 - 19:21
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–.
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Łęczycka-Wilk, Katarzyna; Dąbrowa, Kajetan; Cmoch, Piotr; Jarosz, Sławomir (2017). Chloride-Templated Macrocyclization and Anion-Binding
Properties of C2‑Symmetric Macrocyclic
Ureas from Sucrose. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02198
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AUTHORS (4)
KŁ
Katarzyna Łęczycka-Wilk
KD
Kajetan Dąbrowa
PC
Piotr Cmoch
SJ
Sławomir Jarosz
KEYWORDS
chloride anioncharacterizationAnion-Binding PropertiespredictiontriphosgeneChloride-Templated Macrocyclizationreceptors showbenzoate anionsUreaacetatehexaaffinity1 H NMR titration studiessteric constraintsmacrocycles 33 bMacrocyclictemplationSucrosebenzylmacrocyclizationPOvs 3 bregioisomeric C 2Symmetricone-potsynthesispreference