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Download fileA General Method for Synthesis of Unclosed Cryptands via H‑Bond Templated Macrocyclization and Subsequent Mild Postfunctionalization
journal contribution
posted on 2015-10-02, 00:00 authored by Kajetan Dabrowa, Patryk Niedbala, Maciej Majdecki, Piotr Duszewski, Janusz JurczakA practical four-step synthesis of
a model 26-membered N-Boc-protected
macrocycle, starting from commercially available and inexpensive materials,
is reported. The crucial macrocyclization step does not require high-dilution
conditions and is completed in a short time (8 h). The high yield
of macrocyclization (61%) is achieved owing to templation by intramolecular
H-bonds and a chloride anion, which both help to adopt a favorable
folded conformation of the open-chain intermediate. Finally, mild,
selective, and efficient incorporation of intraannular amide function
leading to five diversely functionalized unclosed cryptands (UCs)
is described.
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Keywords
chloride anionGeneral MethodSubsequent Mild Postfunctionalizationhigh-dilution conditionsopen-chainintraannular amide functionmodel 26- membered N-Boc-protected macrocyclediversely functionalized unclosed cryptandsTemplatedMacrocyclizationfour-step synthesisUnclosed CryptandsmaterialconformationtemplationincorporationUCSynthesimacrocyclization stepintramolecular H-bonds