Synthesis, Structure, and Resolution of Functionalized Oxacalix[4]arenes with Planar Chirality via Dynamic SNAr Reaction

A pair of racemic oxacalix[4]arenes featuring planar chirality and a mesomer with a symmetric plane were conveniently synthesized under mild conditions via a one‐pot dynamic SNAr reaction and separated in 20 % and 49 % yields, respectively. X‐ray single crystal analyses confirmed their structures un...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-10, Vol.27 (37), p.n/a
Main Authors: Yang, Yong, Yu, Yin‐Chong, Xue, Min, Peng, Wei‐Wei, Xue, Bo‐Wen, Zong, Qian‐Shou
Format: Article
Language:English
Subjects:
Dynamic process
Oxacalixarenes
Planar chirality
SNAr reaction
Tautomerism
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Summary:A pair of racemic oxacalix[4]arenes featuring planar chirality and a mesomer with a symmetric plane were conveniently synthesized under mild conditions via a one‐pot dynamic SNAr reaction and separated in 20 % and 49 % yields, respectively. X‐ray single crystal analyses confirmed their structures unambiguously. The racemic mixture could further be resolved using HPLC on a chiral column. Time‐dependent products distribution and interconversion between products with CsF as a catalyst were revealed by 1H NMR studies, convincing the dynamic nature of SNAr reaction. A pair of racemic oxacalix[4]arenes exhibiting planar chirality and a mesomer with a symmetric plane were conveniently synthesized and separated via dynamic SNAr reaction in 20 % and 49 % yields, respectively. The racemic mixture could be further resolved using HPLC on a chiral column. The products interconverted in the presence of CsF as a catalyst.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202400576