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master's thesis
Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2020. urn:nbn:hr:149:113171
Zubčić, Gabrijel
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Zubčić, G. (2020). Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:113171

Zubčić, Gabrijel. "Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2020. https://urn.nsk.hr/urn:nbn:hr:149:113171

Zubčić, Gabrijel. "Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2020. https://urn.nsk.hr/urn:nbn:hr:149:113171

Zubčić, G. (2020). 'Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 26 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:113171

Zubčić G. Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2020 [cited 2024 November 26] Available at: https://urn.nsk.hr/urn:nbn:hr:149:113171

G. Zubčić, "Stereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2020. Available at: https://urn.nsk.hr/urn:nbn:hr:149:113171

Metadata
TitleStereoselektivna arilacija diaril-ketimina katalizirana kiralnim Brønstedovim kiselinama
Title (english)Stereoselective arylation of diaryl-ketimines catalyzed by chiral Brønsted acids
AuthorGabrijel Zubčić
MentorIrena Škorić (mentor)
MentorMatija Gredičak (komentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberLidija Furač (član povjerenstva)
Committee memberMatija Gredičak (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2020-09-21, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U sklopu ovog rada pripravljeni su α-(diaril) izoindolinonski alkoholi (1-5) koji su poslužili kao polazni supstrati za pripravu racemičnih (6-12) i kiralnih (13-19) α-kvaternih triarilmetanamina primjenom formalne Bettijeve reakcije. Provedena je priprava 3-supstituiranih-3-hidroksiizoindolinona upotrebom organometalnih reagensa. Fenilni supstituenti s elektron-donirajućim skupinama (1-2) reagirali su s ftalimidom u Grignardovoj reakciji, dok su elektron-odvlačeće skupine (3-4) zahtijevale litij-brom izmjenu. Izoindolinonski alkohol s tiofenskim supstituentom (5) je sintetiziran strategijom izravne litijacije. Ostali upotrijebljeni alkoholi su već prethodno sintetizirani u Laboratoriju i njihova sinteza nije dio ovog rada. Uslijedila je provedba racemične formalne Bettijeve reakcije, koja uključuje adiciju 2,6-dimetilfenola na in situ generirani α-(diaril)-N-(acil)ketimin iz 3-aril-3-hidroksiizoindolinona (1-5) uz para-toluensulfonsku kiselinu kao katalizator. Dobiveni α-kvaterni triarilmetanamini (6-12) izolirani su u slabim do izvrsnim prinosima. U stereoselektivnoj verziji reakcije kao izvor kiralnosti koristila se kiralna fosforna kiselina (CPA) s binaftilnom okosnicom. Nastali Bettijevi produkti (13-19) izolirani su u slabim do izvrsnim prinosima i umjerenim do visokim vrijednostima enantioselektivnosti.
Abstract (english)
Within this work α-(diaryl) isoindolinone alcohols (1-5) have been prepared and used as inital supstrates for the preparation of racemic (6-12) and chiral (13-19) α-quaternary triarylmethanamines through formal Betti reaction. Preparation of 3-substituted-3-hydroxyisoindolinones was carried out by using organometallic reagents. Phenyl substituents with electron-donating groups (1-2) reacted with phthalimide via the Grignard reaction, while the electron-withdrawing groups required bromine-lithium exchange (3-4). Isoindolinone alcohol with a thiophene substituent was synthesized by direct lithiation strategy (5). Other alcohols where synthesised beforehand in the Lab and their synthesis was not part of this work. In a racemic formal Betti reaction, the addition of 2,6-dimethylphenole to in situ generated α-(diaryl)-N-(acyl)ketimines from 3-aryl-3-hydroxyisoindolinones (1-5) was performed by utilizing para-toluenesulfonic acid as catalyst. Obtained α-quaternary triarylmethanamines (6-12) were isolated in good to excellent yields. In the stereoselective version of the reaction, chiral phosphoric acid (CPA) with binaphthyl framework was used. Obtained Betti products (13-19) were isolated in good to excellent yields, and with moderate to excellent enantioselectivity.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:113171
Study programmeTitle: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2022-04-21 13:04:12