prikaz prve stranice dokumenta Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama
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master's thesis
Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama
Zagreb: University of Zagreb, Faculty of Science, 2020. urn:nbn:hr:217:233925
Talajić, Gregor
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Talajić, G. (2020). Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:233925

Talajić, Gregor. "Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama." Master's thesis, University of Zagreb, Faculty of Science, 2020. https://urn.nsk.hr/urn:nbn:hr:217:233925

Talajić, Gregor. "Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama." Master's thesis, University of Zagreb, Faculty of Science, 2020. https://urn.nsk.hr/urn:nbn:hr:217:233925

Talajić, G. (2020). 'Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama', Master's thesis, University of Zagreb, Faculty of Science, accessed 25 May 2024, https://urn.nsk.hr/urn:nbn:hr:217:233925

Talajić G. Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2020 [cited 2024 May 25] Available at: https://urn.nsk.hr/urn:nbn:hr:217:233925

G. Talajić, "Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2020. Available at: https://urn.nsk.hr/urn:nbn:hr:217:233925

Metadata
TitleStereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama
Title (english)Stereoselective synthesis of aryl derivatives of isoindolinone catalysed by chiral Brønsted acids
AuthorGregor Talajić
MentorMatija Gredičak (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberVladimir Stilinović (član povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberIvana Biljan (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2020-02-27, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U ovome radu prikazana je priprava 3,3-diarilizoindolin-1-ona modificiranom enantioselektivnom Bettijevom reakcijom: asimetričnom organokatalitičkom adicijom fenola na in situ generirane N-acil diarilketimine kataliziranom kiralnom fosfornom kiselinom. Kao stabilni prekursori N-acil diarilketimina korišteni su 3-aril-3-hidroksiizoindolin-1-oni pripravljeni adicijom Grignardovih reagensa i organolitijevih spojeva na ftalimid. Provedene su priprave racemičnih 3,3-diarilizoindolin-1-ona u svrhu potvrde reaktivnosti ovakvih spojeva u modificiranoj Bettijevoj reakciji. Istraženi su utjecaji halogeniranih arilnih skupina i heterocikličkih skupina na položaju 3 izoindolinona na enantioselektivnost i prinos reakcije.Strukture priređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom te spektrometrijom masa dok je stupanj enantioselektivnosti određen tekućinskom kromatografijom visoke djelotvornosti s kiralnom kolonom.
Abstract (english)
An approach to enantioenriched 3,3-diaryl isoindolin-1-ones was developed using the asymmetric chiral phosphoric acid-catalyzed addition of phenols to in situ generated N-acyl diarylketimines. 3-aryl-3-hydroxyisoindolin-1-ones were prepared as stable precursors of the reactive N-acyl diarylketimines by the addition of Grignard reagents and organolithium compounds to phtalimide. The influence of the aryl group on the reaction outcome was studied. 3-aryl 3-hydroxyisoindolin-1-ones are precursors in the synthesis of chiral - triarylmethylamines. The structures of prepared compounds were confirmed by 1H and 13C NMR spectroscopy, as well as mass spectrometry. The enantioselectivity in the products was determined by chiral HPLC.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:233925
Study programmeTitle: Graduate university studies in chemistry; specializations in: Research programme
Course: Research programme
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2022-02-27
Terms of useLicence In copyright icon
Created on2020-03-19 10:55:58