Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom

Degač, Marina

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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

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APA 6th Edition

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

MLA 8th Edition

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

Chicago 17th Edition

Harvard

Degač, M. (2021). 'Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom', Master's thesis, University of Zagreb, Faculty of Science, accessed 25 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:392578

Vancouver

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 December 25] Available at: https://urn.nsk.hr/urn:nbn:hr:217:392578

IEEE

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

Cite this item: https://urn.nsk.hr/urn:nbn:hr:217:392578

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Title	Stereoselektivna priprava beta,beta-diaril-ketona s beta-kvaternim kiralnim centrom
Title (english)	Stereoselective synthesis of beta,beta-diaryl ketones with beta-quaternary stereogenic center
Author	Marina Degač
Mentor	Matija Gredičak (mentor)
Committee member	Vesna Petrović Peroković (predsjednik povjerenstva)
Committee member	Iva Juranović Cindrić (član povjerenstva)
Committee member	Željka Soldin (član povjerenstva)
Committee member	Ivan Kodrin (član povjerenstva)
Granter	University of Zagreb Faculty of Science (Department of Chemistry) Zagreb
Defense date and country	2021-02-26, 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)
Language	croatian
URN:NBN	urn:nbn:hr:217:392578
Project	Number: 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 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: 2023-02-26
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Repository	Repository of the Faculty of Science
Created on	2021-03-18 11:57:12