Sinteza in pretvorbe tetramskih kislin iz glicina

Hozjan, Mišel (author), Grošelj, Uroš (mentor)

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.

• Language: Slovenian
• Keywords: tetramska kislina, trans-β-nitrostiren, benzil bromid, alkiliranje
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2019
• PID: 20.500.12556/RUL-109022
• COBISS.SI-ID: 1538293699
• Publication date in RUL: 19.08.2019

Secondary language

• Language: English
• Title: Synthesis and transformations of glycine-derived tetramic acids

Abstract

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.

• Keywords: tetramic acid, trans-β-nitrostyrene, benzyl bromide, alkylation