U sklopu diplomskog rada pripravljeno je pet derivata 2-kinolinonskih epoksida. Tri disupstituirana epoksida dobivena su reakcijom akiralne benzilsulfonijeve soli i odgovarajućeg aldehida u prisustvu baze, kao smjese cis i trans izomera u dobrom iskorištenju. Ispitan je utjecaj baze i temperature na iskorištenje i dijastereoselektivnost reakcije te je uočeno da baza nema bitan utjecaj na dijastereoselektivnost epoksidacije. U svim slučajevima prevladava trans izomer. Reakcijom izopropil(difenil)sulfonijeve soli i odgovarajućeg aldehida u prisustvu tertbutillitija, pripravljena su dva trisupstituirana epoksida. Na pripravljenoj seriji epoksida ispitani su uvjeti regioselektivnog otvaranja prstena korištenjem azidnih nukleofila. Uočeno je da se najbolja konverzija postiže pri povišenim temperaturama u polarnom sustavu otapala te da regioselektivnost reakcije ovisi o broju supstituenata na epoksidnom prstenu. U drugom dijelu istraživanja ispitani su uvjeti odjeljivanja enantiomera epoksida na polisaharidnim kiralnim nepokretnim fazama primjenom visokodjelotvorne tekućinske kromatografije. Najboljim izborom za odjeljivanje enantiomera pokazala se Chiralpak AD nepokretna faza s tris-(3,5- dimetilfenilkarbamat) amilozom kao kiralnim selektorom. In this thesis, five derivatives of 2-quinolinone epoxides were prepared. Three disubstituted epoxides were obtained by reaction between an achiral benzylsulfonium salt and the corresponding aldehyde in the presence of a base, as a mixture of cis/trans isomers in good yield. The effect of base and temperature on the yield and diastereoselectivity of the reaction was investigated. It was observed that base had no significant effect on the diastereoselectivity of epoxidation. In all cases, the trans isomer predominates. Two trisubstituted epoxides were prepared by reaction between isopropyl(diphenyl)sulfonium salt and the corresponding aldehyde in the presence of tert-butyl-lithium. Conditions for regioselective ring-opening were tested on prepared series of compounds using an azide reagents. It was observed that the best conversion was achieved at higher temperatures in the polar solvent system. The regioselectivity of reaction depends on the number of substituents. In the second part of research, the conditions for the enantioseparation of epoxides on polysaccharide chiral stationary phases were investigated using high performance liquid chromatography. Chiralpak AD stationary phase with chiral selector tris-(3,5-dimethylphenylcarbamate) amylose proved to be the best choice.
