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Updated: Sep 14, 2025

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Published on: September 28, 2022
Strained and Twisted Macrocycles via Folding-Assisted Cyclization of Aromatic Ether ε-Amino Acid Oligomers
Yong Yang1, Wei-Wei Peng1, Bo-Wen Xue2
1School of Chemistry and Chemical Engineering, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou 310018, China.
Abstract:
Twisted and strained macrocycles were synthesized efficiently through condensation of a series of open-chain helical oligo(aromatic ether ε-amino acid) at the sacrifice of the ideal hydrogen bonding pattern present in the linear precursors. Folding-assisted preorganization and the free rotation of terminal aryl groups around the C-O (aromatic ether) axis were identified as key factors enabling such a high cyclization efficiency. X-ray crystallographic analysis revealed the presence of mirror-image conformational enantiomers, the interconversion mechanism of which was further elucidated through DFT calculations.
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