Sinteza tetramske kisline iz Cbz-Gly-OH in uporaba v organokataliziranih 1,4-adicijah

Golob, Ana (author), Grošelj, Uroš (mentor)

Iz Cbz-zaščitenega glicina in Meldrumove kisline sem sintetizirala tetramsko kislino, ki sem jo nato uporabila kot izhodno spojino za pripravo njenih derivatov. Z reakcijo Michaelove adicije sem nanjo adirala trans-β-nitrostiren, pri tem pa sem uporabila dva različna organokatalizatorja, in sicer kiralnega in akiralnega. Produkta Michaelove adicije sem nato alkilirala z benzil bromidom in dobila končna produkta. Eden od njiju je nastal v obliki racemne zmesi, drugi pa je bil enantiomerno obogaten. Enantiomerni presežek slednjega sem določila s pomočjo metode HPLC.

• Language: Slovenian
• Keywords: tetramska kislina, Michaelova adicija, alkiliranje, organokatalizatorji
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2021
• PID: 20.500.12556/RUL-127945
• COBISS.SI-ID: 70466819
• Publication date in RUL: 29.06.2021

Secondary language

• Language: English
• Title: Synthesis of tetramic acid from Cbz-Gly-OH and use in organo catalyzed 1,4-aditions

Abstract

Tetramic acid was synthesized from Cbz-protected glycine and Meldrum's acid. It was then used as a starting compound for the preparation of tetramic acid derivatives, starting with Michael addition of trans-β-nitrostyrene. Two different organocatalysts were used in this step: a chiral and an achiral one. The products of Michael addition were then alkylated with benzyl bromide and the final products were obtained. One of them was formed as a racemic mixture and the other one was enantiomerically enriched. The enantiomeric excess of the latter one was determined with the help of HPLC.

• Keywords: tetramic acid, Michael addition, alkylation, organocatalysts