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doctoral thesis
Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom
Zagreb: University of Zagreb, Faculty of Science, 2022. urn:nbn:hr:217:084383
Beriša, Arben
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Beriša, A. (2022). Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:084383

Beriša, Arben. "Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom." Doctoral thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:084383

Beriša, Arben. "Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom." Doctoral thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:084383

Beriša, A. (2022). 'Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 21 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:084383

Beriša A. Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2022 [cited 2024 December 21] Available at: https://urn.nsk.hr/urn:nbn:hr:217:084383

A. Beriša, "Organokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:217:084383

Metadata
TitleOrganokatalitička stereoselektivna priprava derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom
Title (english)Organocatalytic stereoselective synthesis of isoindolinone derivatives with triaryl substituted quaternary stereogenic center
AuthorArben Beriša
MentorMatija Gredičak (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberIrena Škorić (član povjerenstva)
Committee memberMarina Šekutor (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2022-12-15, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
U sklopu ove doktorske radnje razvijen je protokol koji opisuje sintezu derivata izoindolinona s triaril-supstituiranim kvaternim stereogenim centrom u organokatalitičkim uvjetima. Provedeno je stereoselektivno i regioselektivno ariliranje izoindolinona, te aza-Friedel Craftsova adicija pirola kroz položaj C3. Tako opisane transformacije katalizirane kiralnim fosfornim kiselinama uključuju širok raspon različitih nukleofila i izoindolinonskih alkohola za stvaranje kvaternog stereogenog centra s tri arilna supstituenta u odličnim prinosima i razinama enantioselektivnosti (do 98% prinosa, do 99,5:0,5 e.r.). Mehanizam stereokemijske indukcije predložen je na temelju rezultata dobivenih kvantno-mehaničkim računima i kontrolnim eksperimentima. Ispitana je primjenjivost opisanih metodologija provedbom reakcije na većoj skali i posttransformacijskom reakcijom bez gubitka optičke čistoće.
Abstract (english)
An organocatalytic asymmetric protocol for the synthesis of isoindolione derivatives possessing triaryl-substituted quaternary stereogenic centers is developed. Stereoselective and regioselective arylation of isoindolinones with phenols and pyrroles at C3 position has been carried out. Described stereoselective transformations proceed smoothly with a broad range of arenes and isoindolinone alcohols in reactions mediated by chiral phosphoric acid catalyst to generate triaryl-substituted quaternary stereogenic centers in excellent yields and enantioselectivities (up to 98% yield, up to 99,5:0,5 e.r.). In the order to shed light on the mechanism of stereochemical induction, control experiments and density functional theory calculations have been performed. Applicability of such described methodologies has been investigated by conducting the postmodification and scale-up reaction without loss of optical purity in the products.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:084383
Promotion2023
ProjectNumber: IP-2018-01-4053
Title: Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom
Acronym: NSYNC-ACDC
Leader: Matija Gredičak
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Doctoral study in chemistry
Study programme type: university
Study level: postgraduate
Academic / professional title: doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija (doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija)
Type of resourceText
Extent195 str. ; 30 cm
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2024-12-15
Terms of useLicence In copyright icon
Created on2023-01-13 13:42:01