diplomsko delo
Lara Rems (Author), Uroš Grošelj (Mentor)

Abstract

Iz N-Boc-glicilglicina sem s pomočjo Meldrumove kisline pripravila derivat tetramske kisline. Nato sem tetramski kislini dodala trans-β-nitrostiren, kot Michaelov akceptor, in organokatalizator. V prvem primeru sem za nastanek produkta Michaelove adicije uporabila kiralni katalizator, v drugem primeru pa akiralen katalizator. Dobila sem produkta, kjer se je nitrostiren adiral na nukleofilni ogljik, ki je pozicioniran med karbonilnima skupinama na tetramski kislini. Obe spojini sem nato alkilirala z benzil bromidom in za končni spojini s pomočjo analize HPLC določila pogoje za ločbo enantiomerov ter določila razmerje enantiomerov (enantiomerni presežek). Prvotni derivat tetramske kisline in oba končna alkilirana produkta sem potrdila z NMR, IR in MS analizo.

Keywords

tetramska kislina;Michaelova adicija;bifunkcionalna organokataliza;enantiomerni presežek;trans-ß-nitrostiren;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [L. Rems]
UDC: 547.74(043.2)
COBISS: 111238147 Link will open in a new window
Views: 152
Downloads: 37
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Other data

Secondary language: English
Secondary title: Synthesis of tetramic acid from Boc-Gly-Gly-OH and its use in organocatalyzed addition to trans-β-nitrostyrene derivatives
Secondary abstract: A derivative of tetramic acid was synthesised from N-Boc-glycylglycine. Afterwards, trans-β-nitrostyrene, as the Michael acceptor, was added to the tetramic acid in the presence of an organocatalyst. In the first experiment, I used chiral organocatalyst as opposed to achiral organocatalyst, that was used in the second experiment. Synthesised product was tetramic acid, where nitrostyrene has added to the nucleophilic carbon positioned between the two carbonyl groups of the tetramic acid. After that, I performed alkylation reaction of the two previously obtained products with benzyl bromide as the alkylating reagent. HPLC analysis was used to confirm the racemic mixture in one of the products and to help determine the enantiomeric excess of the product where chiral catalyst was used. The structures of tetramic acid and the two alkylated products were confirmed by NMR, IR, and MS analyses.
Secondary keywords: tetramic acid;Michael addition;bifunctional organocatalysis;enantiomeric excess;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Type (COBISS): Bachelor thesis/paper
Study programme: 1000373
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages: 32 str.
ID: 15563697