Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama

Talajić, Gregor

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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

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APA 6th Edition

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

MLA 8th Edition

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

Chicago 17th Edition

Harvard

Talajić, G. (2020). 'Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama', Master's thesis, University of Zagreb, Faculty of Science, accessed 27 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:233925

Vancouver

Talajić G. Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2020 [cited 2024 November 27] Available at: https://urn.nsk.hr/urn:nbn:hr:217:233925

IEEE

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

Cite this item: https://urn.nsk.hr/urn:nbn:hr:217:233925

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Title	Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama
Title (english)	Stereoselective synthesis of aryl derivatives of isoindolinone catalysed by chiral Brønsted acids
Author	Gregor Talajić
Mentor	Matija Gredičak (mentor)
Committee member	Vesna Petrović Peroković (predsjednik povjerenstva)
Committee member	Vladimir Stilinović (član povjerenstva)
Committee member	Iva Juranović Cindrić (član povjerenstva)
Committee member	Ivana Biljan (član povjerenstva)
Granter	University of Zagreb Faculty of Science (Department of Chemistry) Zagreb
Defense date and country	2020-02-27, 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)
Language	croatian
URN:NBN	urn:nbn:hr:217:233925
Study programme	Title: 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 resource	Text
File origin	Born digital
Access conditions	Open access Embargo expiration date: 2022-02-27
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Repository	Repository of the Faculty of Science
Created on	2020-03-19 10:55:58