Luka Ciber (Avtor), Ana Gorenc (Avtor), Mišel Hozjan (Avtor), Franc Požgan (Avtor), Jurij Svete (Avtor), Helena Brodnik Žugelj (Avtor), Bogdan Štefane (Avtor), Uroš Grošelj (Avtor)

Povzetek

Organocatalyzed Michael addition of N-substituted tetramic acids to nitroalkene acceptors followed by O-alkylation gave polyfunctionalized tetramic acid (31 examples, 59–94% ee). The enantioselectivity of the product was influenced by the N-substituent of the substrate. Quantum chemical methods provided the mechanistic insights of the studied transformation. The preferred reaction pathway follows the model proposed by Pápai et al. Single crystal structure confirmed the absolute configuration, which was in line with the ECD measured and calculated structure. Additionally, a comparative study of the alkylation of a selected tetramic and tetronic acid with trans-β-nitrostyrene is disclosed. Follow-up amidations demonstrated the applicability of this class of compounds for the incorporation into both dipeptide and depsipeptide sequences.

Ključne besede

nekovalentna organokataliza;bifunkcionalni nekovalentni organokatalizatorji;tetramske kisline;tetronske kisline;kvantno kemijske metode;amidiranje;dipeptid;asymmetric organocatalysis;bifunctional noncovalent organocatalysts;tetramic acids;tetronic acids;quantum chemical methods;amidation;dipeptide;

Podatki

Jezik: Angleški jezik
Leto izida:
Tipologija: 1.01 - Izvirni znanstveni članek
Organizacija: UL FKKT - Fakulteta za kemijo in kemijsko tehnologijo
UDK: 547.7:66.097
COBISS: 123873283 Povezava se bo odprla v novem oknu
ISSN: 1615-4150
Št. ogledov: 17
Št. prenosov: 6
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: nekovalentna organokataliza;bifunkcionalni nekovalentni organokatalizatorji;tetramske kisline;tetronske kisline;kvantnokemijske metode;amidiranje;dipeptid;
Vrsta dela (COBISS): Članek v reviji
Strani: str. 3840-3855
Letnik: ǂVol. ǂ364
Zvezek: ǂiss. ǂ22
Čas izdaje: 22 Nov. 2022
DOI: 10.1002/adsc.202200810
ID: 18011586