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Pyrrolidine derivatives in organocatalytic transformations

dc.contributor.advisorSavić, Vladimir
dc.contributor.otherTešević, Vele
dc.contributor.otherFerjančić, Zorana
dc.contributor.otherMaslak, Veselin
dc.contributor.otherNikodinović-Runić, Jasmina
dc.creatorJovanović, Predrag M.
dc.date.accessioned2017-06-17T08:53:11Z
dc.date.available2017-06-17T08:53:11Z
dc.date.available2020-07-03T10:16:23Z
dc.date.issued2017-04-07
dc.identifier.urihttp://eteze.bg.ac.rs/application/showtheses?thesesId=5057
dc.identifier.urihttp://nardus.mpn.gov.rs/handle/123456789/8300
dc.identifier.urihttps://fedorabg.bg.ac.rs/fedora/get/o:15788/bdef:Content/download
dc.identifier.urihttp://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=49041935
dc.description.abstractHiralni, polisupstituisani derivati pirolidina, dobijeni cikloadicionim reakcijama azometinskih ilida, proučavani su kao organokatalizatori u Michael-ovoj reakciji aldehida/ketona i vinil-sulfona. Pod optimalnim reakcionim uslovima, u kojima se koristilo 10 mol % katalizatora u vlažnom metilen-hloridu prinosi reakcija su generalno bili dobri dok je enantioselektivnost varirala dostižući 52 %. Razvijen je efikasan biokatalizator za asimetričnu Michael-ovu adiciju acetaldehida na β- nitrostiren na bazi celih ćelija koja eksprimira 4-oksalokrotonat tautomerazu (4-OT). Utvrđen je optimalan odnos supstrata i biokatalizatora. Kada je kao supstrat korišćen β-nitrostiren dobijena je odlična enantioselektivnost (e.e. >99%) uz prinos reakcije do 60%. Biokatalizator je manje efikasan sa p-hlor-, o-hlor- i p-fluor-β-nitrostirenom gde su dobijeni prinosi od 38%, 51%, 31% i e.e. 84%, 88%, 94%...sr
dc.description.abstractChiral, polysubstituted pirrolydines derivatives, obtained via cycloaddition reactions of azomethine ylides, were studied as organocatalysts in the Michael reaction of aldehydes/ketones and vinylsulphones. Under optimised reaction conditions employing 10 mol % of the catalyst in wet CH2Cl2, the yields of the products were generally good while the enantioselectivity varied, reaching up to 52 %. A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to β-nitrostyrenes. Optimal ratio of substrates and biocatalyst was determined. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with β-nitrostyrene substrate. The biocatalyst exhibited lower reaction rates with pchloro-, o-chloro- and p-fluoro-β-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively...en
dc.formatapplication/pdf
dc.languagesr
dc.publisherУниверзитет у Београду, Хемијски факултетsr
dc.rightsopenAccessen
dc.sourceУниверзитет у Београдуsr
dc.subjectorganokatalizasr
dc.subjectorganocatalysisen
dc.subjectproline derivativesen
dc.subjectthiourea derivativesen
dc.subject4-Oxalocrotonate tautomeraseen
dc.subjectMichael reactionen
dc.subjectenantioselectivityen
dc.subjectbiocatalysisen
dc.subjectEscherichia colien
dc.subjectderivati prolinasr
dc.subjectderivati tioureesr
dc.subject4-oksalokrotonat tautomerazasr
dc.subjectMichael-ova reakcijasr
dc.subjectenantioselektivnostsr
dc.subjectbiokatalizasr
dc.subjectEscherichia colisr
dc.titlePirolidinski derivati u organokatalitičkim transformacijamasr
dc.title.alternativePyrrolidine derivatives in organocatalytic transformationsen
dc.typedoctoralThesis
dc.rights.licenseBY-NC-ND
dcterms.abstractСавић, Владимир; Ферјанчић, Зорана; Никодиновић-Рунић, Јасмина; Тешевић, Веле; Маслак, Веселин; Јовановић, Предраг М.; Пиролидински деривати у органокаталитичким трансформацијама; Пиролидински деривати у органокаталитичким трансформацијама;
dc.identifier.fulltexthttp://nardus.mpn.gov.rs/bitstream/id/30386/Disertacija.pdf
dc.identifier.fulltexthttp://nardus.mpn.gov.rs/bitstream/id/30387/IzvestajKomisije10980.pdf


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