Stereoselektivna priprava arilnih derivata izoindolinona katalizirana kiralnim Brønstedovim kiselinama

master's thesis

• 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: Bettijeva reakcija; 3; 3-diarilizoindolin-1-oni; kiralna fosforna kiselina; organokataliza; steroselektivna sinteza
• Keywords (english): Chiral Brønsted acid; diaryl isoindolinone; organocatalysis; stereoselective synthesis
• 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
• Created on: 2020-03-19 10:55:58