magistrsko delo
Mišel Hozjan (Author), Uroš Grošelj (Mentor), Mitja Kolar (Thesis defence commission member), Bogdan Štefane (Thesis defence commission member)

Abstract

Izvedel sem organokatalizirano asimetrično reakcijo Michaelove adicije iz N-Boc-glicina pridobljene tetramske kisline na različne derivate trans-β-nitrostirena. Produkte adicije sem alkiliral z raznimi alkilirnimi sredstvi, predvsem pa z benzil bromidom. Reakcije so potekle enantioselektivno (% ee od 81 do 94). Uspešno sem asimetrično adiral tudi iz N-Boc-glicilglicilglicina pridobljeno tetramsko kislino na trans-β-nitrostiren. Po alkiliranju z benzil bromidom sem produktu določil 59 % ee. Izbranim produktom sem odstranil Boc zaščitno skupino in jih poskusil kristalizirati z namenom pridobitve monokristalov. S pomočjo elektrofilnega fluoriranja sem vnesel fluor v derivat tetramske kisline. Tvoril sem amid s pripravljenim karboksilnim derivatom tetramske kisline s pomočjo in situ aktivacije in dodatkom aminokisline. Poskusil sem tudi asimetrično adirati tetramsko kislino na benzilidenmalononitril v prisotnosti organokatalizatorja, vendar mi je uspelo pridobiti le racemni produkt.

Keywords

organokataliza;organokatalizirane pretvorbe;bifunkcionalna kataliza;tetramska kislina;trans-ß-nitrostiren;zaščitne skupine;sinteza amidov;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [M. Hozjan]
UDC: 547:544.47(043.2)
COBISS: 79683843 Link will open in a new window
Views: 422
Downloads: 80
Average score: 0 (0 votes)
Metadata: JSON JSON-RDF JSON-LD TURTLE N-TRIPLES XML RDFA MICRODATA DC-XML DC-RDF RDF

Other data

Secondary language: English
Secondary title: Use of tetramic acids as starting substrates in organocatalyzed conversions
Secondary abstract: I carried out organocatalysed asymmetric Michael addition involving N-Boc derived tetramic acid and different trans-β-nitrostyrene derivatives. The products of addition were alkylated with different alkylating agents, but mostly with benzyl bromide. Reactions were enantioselective (% ee from 81 to 94). I also successfully asimmetrically added from N-Boc-glycylglycylglycine prepared tetramic acid to trans-β-nitrostyrene. After alkylating the product with benzyl bromide, the enantioselectivity was determined to be 59 %. For selected products, I removed the Boc protecting group and tried crystallising them in order to obtain monocrystals. With the help of electrophilic fluorination I introduced fluorine into a derivate of tetramic acid. I synthesized an amide from the carboxylic acid derivate of tetramic acid using in situ activation and addition of an amino acid. I also tried to asymmetrically add tetramic acid to benzylidene-malononitrile catalyzed by organocatalyst, but I only managed to prepare a racemic product.
Secondary keywords: organocatalysis;bifunctional catalysis;tetramic acid;trans-ß-nitrostyrene;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages: 78 str.
ID: 13324779