Totalna sinteza halogeniranih derivata marinoaziridina

master's thesis

• Title (english): Total syntehesis of halogenated marinoaziridine derivatives
• Author: Marija Renić
• Mentor: Marin Roje (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Ivica Đilović (član povjerenstva)
• Committee member: Adriana Kenđel (član povjerenstva)
• Committee member: Nikola Cindro (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2021-07-16, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U sklopu diplomskog rada razvijena je metoda sinteze halogeniranih derivata marinoaziridina. Strukturni derivati 8a-8h pripravljeni su reakcijom različito supstituiranih N-tosil imina 7a-7h i akiralne 2-kinolinonske sulfonijeve soli 6 u prisustvu baze, kao smjese cis i trans izomera u dobrom iskorištenju. Ispitan je utjecaj baze, temperature i iminskog supstituenta na iskorištenje i dijastereoselektivnost reakcije. Uočeno je da baza nema bitan utjecaj na dijastereoselektivnost aziridinacije.... More Dijastereoselektivnost reakcije je različita i ovisna je o iminskom supstituentu. U većini slučajeva prevladava trans izomer, dok je neobična cis dijastereoselektivnost uočena kod derivata 8d. U drugom dijelu istraživanja ispitani su uvjeti odjeljivanja enantiomera novosintetiziranih spojeva na polisaharidnim kiralnim nepokretnim fazama temeljenim na derivatima amiloze i celuloze primjenom visokodjelotvorne tekućinske kromatografije. Chiral ART Cellulose SC nepokretna faza sa selektorom tris-(3,5-diklorfenilkarbamat) celulozom pokazala se najboljim izborom u odjeljivanju enantiomera, ali i u odjeljivanju cis i trans izomera. Less

Abstract (english)

In this thesis, a method of synthesis of halogenated marinoaziridine derivatives was developed. Structural derivatives 8a-8h were prepared by reaction of variously substituted N-tosyl imines 7a-7h and achiral 2-quinolinone sulfonium salt 6 in the presence of a base, as a mixture of cis and trans isomers in good yield. The effect of base, temperature and imine substituent on the yield and diastereoselectivity of the reaction was investigated. It was observed that the base had no significant... More effect on the diastereoselectivity of aziridination. The diastereoselectivity of the reaction is different and depends on the imine substituent. In most cases, the trans isomer predominates, while unusual cis diastereoselectivity was observed in derivative 8d. In the second part of this research, the conditions of enantioseparation of newly synthesized compounds on polysaccharide chiral stationary phases based on amylose and cellulose derivatives were investigated using high performance liquid chromatography. Chiral ART Cellulose SC stationary phase with selector cellulose tris-(3,5-dichlorophenylcarbamate) proved to be the best choice in the enantioseparation, but also in the separation of cis and trans isomers. Less

• Keywords: enantiomeri; dijastereoizomeri; 2-kinolinoni; marinoaziridini; N-tosil imini; sumporovi ilidi; totalna sinteza
• Keywords (english): enantiomers; diastereoisomers; marinoaziridine; N-tosyl imine; 2-quinolinone; sulfonium ylides; total synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:217:580416
• Project: Number: N/A; Title: Znanstveni centar izvrsnosti za bioprospecting mora; Title: Scientific Center of Excellence for Bioprospecting of the sea; Acronym: BioProCro; Leader: Rozelinda Čož-Rakovac; Jurisdiction: Croatia; Funder: MZOS; Funding stream: ZCI
• 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: 2022-07-16
• Created on: 2021-09-10 11:02:56