magistrsko delo
Erik Trobec (Author), Uroš Grošelj (Mentor), Jurij Lah (Thesis defence commission member), Krištof Kranjc (Thesis defence commission member)

Abstract

Iz tetramske kisline smo sintetizirali alkilirane derivate in optimizirali reakcijske pogoje za optimalno enantioselektivnost v kiralni sintezi. Sintezno pot smo začeli s pretvorbo Boc-zaščitenega glicina (1) in Meldrumove kisline v tetramsko kislino 2. Sledila je Michaelova adicija trans-β-nitrostirena v prisotnosti akiralnega organokatalizatorja in nastanek terc-butil 4-hidroksi-3-(1-fenil-2-nitroetil)-2-okso-2,5-dihidro-1H-pirol-1karboksilata (3). V naslednjem koraku smo produkt 3 z različnimi reagenti RX O-alkilirali in pripravili knjižico alkiliranih derivatov 4. Sintezo izbranega derivata 4.5 smo nato izvedli z različnimi kiralnimi organokatalizatorji. Sintezo v prisotnosti najbolj učinkovitega organokatalizatorja smo nato ponovili v različnih organskih topilih in optimizirali reakcijske pogoje. V zadnji stopnji smo pod optimiziranimi pogoji v prisotnosti akiralnega organokatalizatorja reakcijo izvedli še z izbranimi substituiranimi derivati trans-β-nitrostirena.

Keywords

organska sinteza;organske reakcije;organokataliza;piroloni;tetramska kislina;Michaelova adicija;trans-ß-nitrostiren;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [E. Trobec]
UDC: 547.74:66.097(043.2)
COBISS: 51085827 Link will open in a new window
Views: 529
Downloads: 190
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: Organocatalysed synthesis of alkylated tetramic acid derivatives
Secondary abstract: We synthesized alkylated tetramic acid derivatives and optimized the reaction conditions for the optimal enantioselectivity of the model reaction. We started the synthetic pathway with the transformation of Boc-protected glycine (1) and Meldrum's acid into tetramic acid 2. It was followed by Michael addition of trans-β-nitrostyrene in the presence of achiral organic catalyst, resulting in the formation of tert-butyl 4hydroxy-3-(1-phenyl-2-nitroethyl)-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (3). In the next step, we alkylated the hydroxyl group of compound 3 with various alkylating reagents RX and thus prepared a group of O-alkylated derivatives 4. Then we performed a stereoselective synthesis of a selected derivative 4.5 with various chiral organic catalysts. We repeated the synthesis in the presence of the optimal organocatalyst in various organic solvents, resulting in optimized reaction conditions. In the last step, we peformed a reaction with substituted derivatives of trans-β-nitrostyrene in the presence of achiral organocatalyst under optimized reaction conditions.
Secondary keywords: pyrrolones;tetramic acid;Michael addition;trans-ß-nitrostyrene;organocatalysis;
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: 80 str.
ID: 12512671