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

Abstract

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.

Keywords

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;

Data

Language: English
Year of publishing:
Typology: 1.01 - Original Scientific Article
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
UDC: 547.7:66.097
COBISS: 123873283 Link will open in a new window
ISSN: 1615-4150
Views: 17
Downloads: 6
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Other data

Secondary language: Slovenian
Secondary keywords: nekovalentna organokataliza;bifunkcionalni nekovalentni organokatalizatorji;tetramske kisline;tetronske kisline;kvantnokemijske metode;amidiranje;dipeptid;
Type (COBISS): Article
Pages: str. 3840-3855
Volume: ǂVol. ǂ364
Issue: ǂiss. ǂ22
Chronology: 22 Nov. 2022
DOI: 10.1002/adsc.202200810
ID: 18011586