{"title":"Novel chiral Tetraazacalix[4]arene[2]triazine-based derivatives as catalysts: enantioselective Michael reaction of nitroolefins and diketones","authors":"Hayriye Nevin Genc","doi":"10.1007/s10847-023-01186-1","DOIUrl":null,"url":null,"abstract":"<div><p>A novel derivatives of tetraazacalix[4]arene[2]triazine-based catalysts for enantioselective Michael addition reactions of nitroolefins and diketones were presented. Chiral moieties were connected to the heteroatom-bridged calix-triazin scaffold by reactions of (<i>S</i>)- or (<i>R</i>)-(+)-1-(1-Naphthyl)ethylamine with tetraazacalix[4]arene[2]triazine. To utilize the catalytic activity of the chiral catalysts, diketones reacted with a wide variety of trans-<i>β</i>-nitrostyrenes in Toluene, respectively, obtaining the Michael products in excellent yields and enantiomeric excesses (up to 96% yield and 99% <i>ee</i>).</p><h3>Graphical abstract</h3>\n <figure><div><div><div><picture><source><img></source></picture></div></div></div></figure>\n </div>","PeriodicalId":54324,"journal":{"name":"Journal of Inclusion Phenomena and Macrocyclic Chemistry","volume":"103 5-6","pages":"189 - 199"},"PeriodicalIF":1.7000,"publicationDate":"2023-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s10847-023-01186-1.pdf","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/s10847-023-01186-1","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
A novel derivatives of tetraazacalix[4]arene[2]triazine-based catalysts for enantioselective Michael addition reactions of nitroolefins and diketones were presented. Chiral moieties were connected to the heteroatom-bridged calix-triazin scaffold by reactions of (S)- or (R)-(+)-1-(1-Naphthyl)ethylamine with tetraazacalix[4]arene[2]triazine. To utilize the catalytic activity of the chiral catalysts, diketones reacted with a wide variety of trans-β-nitrostyrenes in Toluene, respectively, obtaining the Michael products in excellent yields and enantiomeric excesses (up to 96% yield and 99% ee).
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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