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

Povzetek

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.

Ključne besede

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

Podatki

Jezik: Slovenski jezik
Leto izida:
Tipologija: 2.11 - Diplomsko delo
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
Založnik: [L. Rems]
UDK: 547.74(043.2)
COBISS: 111238147 Povezava se bo odprla v novem oknu
Št. ogledov: 152
Št. prenosov: 37
Ocena: 0 (0 glasov)
Metapodatki: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Ostali podatki

Sekundarni jezik: Angleški jezik
Sekundarni naslov: Synthesis of tetramic acid from Boc-Gly-Gly-OH and its use in organocatalyzed addition to trans-β-nitrostyrene derivatives
Sekundarni povzetek: 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.
Sekundarne ključne besede: tetramic acid;Michael addition;bifunctional organocatalysis;enantiomeric excess;Organska sinteza (kemija);Univerzitetna in visokošolska dela;
Vrsta dela (COBISS): Diplomsko delo/naloga
Študijski program: 1000373
Konec prepovedi (OpenAIRE): 1970-01-01
Komentar na gradivo: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Strani: 32 str.
ID: 15563697