20.500.12556/RUL-109022 Sinteza in pretvorbe tetramskih kislin iz glicina Synthesis and transformations of glycine-derived tetramic acids Boc-glicin sem s pomočjo Meldrumove kisline pretvoril v tetramsko kislino. Cilj je bil C-alkilirati tetramsko kislino z benzil bromidom v prisotnosti baze in s pomočjo organokatalizatorja adirati trans-β-nitrostiren preko Michaelove adicije. Uporabil sem dva organokatalizatorja: akiralnega in kiralnega. Prvotno sem alkiliral z benzil bromidom. Pri alkiliranju je prišlo večinoma do C- in O-di-alkiliranja, le malo produkta pa je bilo željenega C-mono-alkiliranega. Na C-mono-alkiliran produkt sem nato poizkusil adirati trans-β-nitrostiren s pomočjo akiralnega organokatalizatorja, vendar reakcija ni potekla. Nato sem na izhodno tetramsko kislino s pomočjo organokatalizatorja najprej adiral trans-β-nitrostiren. Pri uporabi obeh katalizatorjih se je le-ta vezal na C atom med karbonilnima skupinama. Produkta sem nato alkiliral z benzil bromidom pri čemer je prišlo do O-alkiliranja. Končnim produktom sem s pomočjo metode HPLC določil enantiomerni presežek ter vse dobljene produkte okarakteriziral. Boc-glycine was converted with the help of Meldrum's acid into the corresponding tetramic acid. The goal was to C-alkylate tetramic acid with benzyl bromide in the presence of a base and/or to add trans-β-nitrostyrene via Michael addition using an organocatalyst. Two different organocatalysts were used: an achiral and a chiral one. Firstly, the tetramic acid was alkylated with benzyl bromide. The major isolated product was C- and O-di-alkylated compound, while the desired C-mono-alkylated compound represented only the minor product. The C-mono-alkylated product was further reacted with trans-β-nitrostyrene in the presence of an achiral organocatalyst but no reaction occurred. Therefore, trans-β-nitrostyrene was first attached to the tetramic acid in the presence of an organocatalysts. Both organocatalysts successfully catalyzed the reaction. Next, the product of the Michael addition was alkylated with benzyl bromide. Exclusively O-alkylation occurred. With the help of HPLC, enantiomeric excess for the final products were determined and all the products were fully characterized. tetramska kislina trans-β-nitrostiren benzil bromid alkiliranje tetramic acid trans-β-nitrostyrene benzyl bromide alkylation true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2019-08-19 13:40:15 2019-08-19 13:40:17 2022-08-21 03:39:26 0000-00-00 00:00:00 2019 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 6126 1538293699 Hozjan_Misel_-_Sinteza_in_pretvorbe_tetramskih_kislin_iz_glicina.pdf Hozjan_Misel_-_Sinteza_in_pretvorbe_tetramskih_kislin_iz_glicina.pdf 1 D2ED8E6C511445EA412BC4E4F5F6D1BE 9cb7245f40d7f3516a4b1254c3491b6255fdd8e3cdd45505a2c91ac14966f673 c2702a05-a1b6-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=120315 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0