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master's thesis
Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom
Zagreb: University of Zagreb, Faculty of Science, 2021. urn:nbn:hr:217:392578
Degač, Marina
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Degač, M. (2021). Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:392578

Degač, Marina. "Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:392578

Degač, Marina. "Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom." Master's thesis, University of Zagreb, Faculty of Science, 2021. https://urn.nsk.hr/urn:nbn:hr:217:392578

Degač, M. (2021). 'Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom', Master's thesis, University of Zagreb, Faculty of Science, accessed 26 November 2024, https://urn.nsk.hr/urn:nbn:hr:217:392578

Degač M. Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2021 [cited 2024 November 26] Available at: https://urn.nsk.hr/urn:nbn:hr:217:392578

M. Degač, "Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:217:392578

Metadata
TitleStereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom
Title (english)Stereoselective synthesis of beta,beta-diaryl ketones with beta-quaternary stereogenic center
AuthorMarina Degač
MentorMatija Gredičak (mentor)
Committee memberVesna Petrović Peroković (predsjednik povjerenstva)
Committee memberIva Juranović Cindrić (član povjerenstva)
Committee memberŽeljka Soldin (član povjerenstva)
Committee memberIvan Kodrin (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2021-02-26, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U ovom diplomskom radu opisane su stereoselektivne priprave β,β-diaril-ketona s β-kvaternim stereogenim centrom. Pripremljeni su racemični i enantiomerno obogaćeni β,β-diaril-ketoni izoindolinonskog motiva. Početni reagensi, 3-arilizoindolinonski alkoholi (4-9) priređeni su Grignardovom reakcijom iz komercijalno dostupnog ftalimida. Iz priređenih alkohola i odabranih ketona u prisutnosti p-toluensulfonske kiseline pripremljeni su racemični β,β-diaril-ketoni s jednim (rac-10-rac-14) ili s dva stereogena centra (rac-15-rac-17). Enantiomerno obogaćeni β,β-diaril-ketoni s jednim (10-14) ili s dva (15-17) stereogena centra pripremljeni su iz istih alkohola i ketona, ali uz dodatak kiralnog katalizatora. Strukture svih priređenih spojeva određene su pomuću spektroskopije NMR (1H i 13C NMR), dok je enantiomerni višak u produktima određen HPLC-om s kiralnom stacionarnom fazom.
Abstract (english)
In this diploma thesis stereoselective synthesis of β,β-diaryl-ketones with β-quaternery stereogenic centre is described. Racemic and enantiomerically enriched β,β-diaryl-ketones with isoindolinone motif were prepared. Starting reagents, 3-aryl-3-hydroxyisoindolinones (4-9) are prepared by Grignard reaction from commercially available phthalimides. Racemic β,β-diaryl-ketones with one steregenic center (rac-10-rac-14) or two stereogenic centers (rac-15-rac-17) are prepared from isoindolinone alcohols (4-9) and corresponding ketones in the presence of p-toluenesulfonic acid. Enantiomerically enriched β,β-diaryl-ketones with one (10-14) or two (15-17) stereogenic centers are prepared from isoindolinone alcohols (4-9) and corresponding ketones with the addition of a chiral catalyst. The structures of all prepared compounds were determined by NMR (1H i 13C) spectroscopy, and the enantiomeric excess in the products was determined by HPLC with chiral stationary phase.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:392578
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: 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 resourceText
File originBorn digital
Access conditionsOpen access
Embargo expiration date: 2023-02-26
Terms of useLicence In copyright icon
Created on2021-03-18 11:57:12