An Approach to Optically Pure Bridging Chiral p-tert-Butylcalix[4]arenes through a Homologous Anionic Ortho-Fries Rearrangement

An Approach to Optically Pure Bridging Chiral p-tert-Butylcalix[4]arenes through a Homologous Anionic Ortho-Fries Rearrangement

A novel efficient approach to optically pure bridging chiral calix[4]­arenes through a homologous anionic ortho-Fries rearrangement of inherently chiral calix[4]­arenes was presented for the first time. As a result, two pairs of N,N′-dimethylformamidyl-substituted bridging chiral p-tert-butylcalix­[...

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Veröffentlicht in:Journal of organic chemistry 2016-11, Vol.81 (22), p.10683-10687
Hauptverfasser: Xu, Wen-Qiang, Liu, Wen-Shan, Yan, Jiu-Xing, Ma, Shi-Kun, Guo, Jing, Liu, Jun-Min, Wang, Run-Ling, Li, Shao-Yong
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel efficient approach to optically pure bridging chiral calix[4]­arenes through a homologous anionic ortho-Fries rearrangement of inherently chiral calix[4]­arenes was presented for the first time. As a result, two pairs of N,N′-dimethylformamidyl-substituted bridging chiral p-tert-butylcalix­[4]­arene enantiomers were facilely obtained. Their absolute configurations were determined through ROESY analysis, ECD comparison, and X-ray crystallographic analysis.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01682