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

master's thesis

• 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: adicija enola; 3-aril-3-hidroksiizoindolinon; Brønstedova kiselina; β; β-diaril-keton; ketimin
• Keywords (english): 3-aryl-3-hidroxyisoindolinone; β; β-diaryl-ketone; Brønsted acid; enole addition; ketimine; stereogenic center
• 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
• Created on: 2021-03-18 11:57:12