{"title":"Synthesis and organocatalytical evaluation of optically pure inherently chiral calix[4]arene phosphoric acids","authors":"Andrii Karpus, Oleksandr Yesypenko, Jean-Claude Daran, Zoia Voitenko, Eric Manoury, Vitaly Kalchenko","doi":"10.1007/s10847-024-01267-9","DOIUrl":null,"url":null,"abstract":"<div><p>Two pairs of diastereomerically pure calix[4]arene phosphoric acid derivatives with ABHH and ABCH substitution patterns were synthesized via phosphorylation and phosphotropic rearrangement on the narrow rim. These new cone-shaped, inherently chiral calixarenes were tested as organocatalysts in the stereoselective aza-Diels–Alder reaction of imines with Danishefsky's diene, as well as in the stereoselective epoxide ring opening.</p></div>","PeriodicalId":638,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"105 1-2","pages":"75 - 86"},"PeriodicalIF":1.6000,"publicationDate":"2024-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10847-024-01267-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Agricultural and Biological Sciences","Score":null,"Total":0}
引用次数: 0
Abstract
Two pairs of diastereomerically pure calix[4]arene phosphoric acid derivatives with ABHH and ABCH substitution patterns were synthesized via phosphorylation and phosphotropic rearrangement on the narrow rim. These new cone-shaped, inherently chiral calixarenes were tested as organocatalysts in the stereoselective aza-Diels–Alder reaction of imines with Danishefsky's diene, as well as in the stereoselective epoxide ring opening.
期刊介绍：
The Journal of Inclusion Phenomena and Macrocyclic Chemistry is the premier interdisciplinary publication reporting on original research into all aspects of host-guest systems. Examples of specific areas of interest are: the preparation and characterization of new hosts and new host-guest systems, especially those involving macrocyclic ligands; crystallographic, spectroscopic, thermodynamic and theoretical studies; applications in chromatography and inclusion polymerization; enzyme modelling; molecular recognition and catalysis by inclusion compounds; intercalates in biological and non-biological systems, cyclodextrin complexes and their applications in the agriculture, flavoring, food and pharmaceutical industries; synthesis, characterization and applications of zeolites.
The journal publishes primarily reports of original research and preliminary communications, provided the latter represent a significant advance in the understanding of inclusion science. Critical reviews dealing with recent advances in the field are a periodic feature of the journal.
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