Enantioselective organocatalyzed functionalization of tetramic and tetronic acids

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

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.

• Language: English
• Keywords: asymmetric organocatalysis, bifunctional noncovalent organocatalysts, tetramic acids, tetronic acids, quantum chemical methods, amidation, dipeptide
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2022
• Number of pages: Str. 3840-3855
• Numbering: Vol. 364, iss. 22
• PID: 20.500.12556/RUL-144335
• UDC: 547.7:66.097
• ISSN on article: 1615-4150
• DOI: 10.1002/adsc.202200810
• COBISS.SI-ID: 123873283
• Publication date in RUL: 15.02.2023

Record is a part of a journal

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

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: nekovalentna organokataliza, bifunkcionalni nekovalentni organokatalizatorji, tetramske kisline, tetronske kisline, kvantnokemijske metode, amidiranje, dipeptid

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza