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doctoral thesis
Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom
Zagreb: University of Zagreb, Faculty of Science, 2022. urn:nbn:hr:217:161509
Matišić, Mateja
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Matišić, M. (2022). Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom (Doctoral thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:161509

Matišić, Mateja. "Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom." Doctoral thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:161509

Matišić, Mateja. "Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom." Doctoral thesis, University of Zagreb, Faculty of Science, 2022. https://urn.nsk.hr/urn:nbn:hr:217:161509

Matišić, M. (2022). 'Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom', Doctoral thesis, University of Zagreb, Faculty of Science, accessed 31 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:161509

Matišić M. Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom [Doctoral thesis]. Zagreb: University of Zagreb, Faculty of Science; 2022 [cited 2024 December 31] Available at: https://urn.nsk.hr/urn:nbn:hr:217:161509

M. Matišić, "Stereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom", Doctoral thesis, University of Zagreb, Faculty of Science, Zagreb, 2022. Available at: https://urn.nsk.hr/urn:nbn:hr:217:161509

Metadata
TitleStereoselektivna priprava β,β-diaril-ketona s β-tetrasupstituiranim stereogenim centrom
Title (english)Stereoselective synthesis of β,β-diaryl ketones with β-tetrasubstituted stereogenic center
AuthorMateja Matišić
MentorMatija Gredičak (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberŽeljka Soldin (član povjerenstva)
Committee memberIrena Dokli (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2022-07-15, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Universal decimal classification
(UDC)		54 - Chemistry. Crystallography. Mineralogy
Abstract
Metodologije priprave kiralnih β,β-diaril ketona temelje se uglavnom na arilacijama 1,4- nezasićenih ketona u prisutnosti kiralnih kompleksa prijelaznih metala kao katalizatora. Iako u većini slučajeva generiraju tercijarni centar kiralnosti na β-ugljikovom atomu, u literaturi postoji nekoliko primjera gdje je moguće pripraviti tetrasupstituirani stereocentar na tom ugljikovom atomu. U sklopu ove disertacije razvijena je organokatalitička metodologija stereoselektivne priprave izoindolinonskih derivata β,β-diaril ketona s jednim kvaternim, odnosno dva vicinalna stereogena centra u prinosima 35‒98 % s visokom enantioselektivnošću (e.r. = 60:40 ‒ >99:1). Na dobivenim su produktima uspješno provedene izabrane transformacijske reakcije bez gubitka optičke čistoće.
Abstract (english)
Methodologies for the enantioselective synthesis of chiral β,β-diaryl ketones are mainly based on the transition metal-catalyzed arylations of 1,4-unsaturated ketones. Most strategies for accessing these compounds yield products with tertiary stereocenters, however, there are several examples in the literature for the contruction of a tetrasubstituted (gem)-diarylalkyl center of chirality. Within this dissertation, an organocatalytic methodology for the stereoselective preparation of isoindolinone-derived β,β-diaryl ketones with one quaternary, and two vicinal stereogenic centers is developed. Products were prepared in 35‒98% yields with high enantioselectivity (e.r. = 60:40 ‒ 99:1). Obtained products successfully underwent postmodification reactions without loss of optical purity.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:161509
Promotion2022
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
Extent151 str. ; 30 cm
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2022-10-03 16:46:45