折叠辅助环化芳醚ε-氨基酸低聚物的张力和扭曲大环。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-21 DOI:10.1021/acs.joc.5c01470

Yong Yang,Wei-Wei Peng,Bo-Wen Xue,Min Xue

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引用次数: 0

摘要

通过一系列开链螺旋低聚物（芳香醚ε-氨基酸）的缩合，以牺牲线性前驱体中存在的理想氢键模式为代价，有效地合成了扭曲和应变大环。折叠辅助预组织和末端芳基围绕C-O（芳香醚）轴的自由旋转被认为是实现如此高环合效率的关键因素。x射线晶体学分析揭示了镜像构象对映体的存在，并通过DFT计算进一步阐明了其相互转化机理。

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Strained and Twisted Macrocycles via Folding-Assisted Cyclization of Aromatic Ether ε-Amino Acid Oligomers.

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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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.