Luka Ciber (Avtor), Sebastijan Ričko (Avtor), Jure Gregorc (Avtor), Franc Požgan (Avtor), Jurij Svete (Avtor), Helena Brodnik Žugelj (Avtor), Bogdan Štefane (Avtor), Uroš Grošelj (Avtor)

Povzetek

Arylidene-Δ2-pyrrolin-4-ones undergo organocatalyzed annulation with malononitrile, furnishing dihydropyrano[3,2-b]pyrroles (18 examples, 0–77% ee in dichloromethane, 11–44% ee in methanol). The products could be enantiomerically enriched by trituration (11 examples, 95–99% ee). Enantioselectivity was dependent on the nature of the substrate and the conformation of the catalyst, which in turn was solvent-controlled. The reaction mechanism, which included two pseudo-enantiomeric organocatalyst conformations, was investigated by experimental and quantum chemical methods. The reaction mechanism consists of Michael addition reaction step followed by 6-exo-dig annulation, which was found to be the rate determining step. Additionally, it was identified that the preferred reaction pathway follows the model originally proposed by Pápai et al.

Ključne besede

organokataliza;asimetrična sinteza;enantioselektivnost;učinki topil;piroloni;psevdo-enantiomerne konformacije katalizatorja;organocatalysis;asymmetric synthesis;enantioselectivity;solvent effects;pyrrolone;pseudo-enantiomeric catalyst conformations;

Podatki

Jezik: Angleški jezik
Leto izida:
Tipologija: 1.01 - Izvirni znanstveni članek
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
UDK: 547.74:544.47
COBISS: 97278211 Povezava se bo odprla v novem oknu
ISSN: 1615-4150
Št. ogledov: 204
Št. prenosov: 15
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: Slovenski jezik
Sekundarne ključne besede: organokataliza;asimetrična sinteza;enantioselektivnost;učinki topil;piroloni;psevdo-enantiomerne konformacije katalizatorja;
Vrsta dela (COBISS): Članek v reviji
Konec prepovedi (OpenAIRE): 2023-01-14
Strani: str. 980-993
Letnik: ǂVol. ǂ364
Zvezek: ǂiss. ǂ5
Čas izdaje: 1 Mar. 2022
DOI: 10.1002/adsc.202101369
ID: 14536735