Enantioselective organocatalyzed functionalization of tetramic and tetronic acids

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

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.

• Jezik: Angleški jezik
• Ključne besede: asymmetric organocatalysis, bifunctional noncovalent organocatalysts, tetramic acids, tetronic acids, quantum chemical methods, amidation, dipeptide
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2022
• Št. strani: Str. 3840-3855
• Številčenje: Vol. 364, iss. 22
• PID: 20.500.12556/RUL-144335
• UDK: 547.7:66.097
• ISSN pri članku: 1615-4150
• DOI: 10.1002/adsc.202200810
• COBISS.SI-ID: 123873283
• Datum objave v RUL: 15.02.2023

Gradivo je del revije

• Naslov: Advanced synthesis & catalysis
• Založnik: Wiley
• ISSN: 1615-4150
• COBISS.SI-ID: 22726149

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: nekovalentna organokataliza, bifunkcionalni nekovalentni organokatalizatorji, tetramske kisline, tetronske kisline, kvantnokemijske metode, amidiranje, dipeptid

Projekti

• Financer: ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
• Številka projekta: P1-0179
• Naslov: Napredna organska sinteza in kataliza