Synthesis and organocatalytic activity of imidazolidinone organocatalysts

Petek, Nejc (author), Ciber, Luka (author), Golobič, Amalija (author), Mihevc, Andrej (author), Požgan, Franc (author), Svete, Jurij (author), Štefane, Bogdan (author), Grošelj, Uroš (author)

series of cis-5-arylmethyl-2-alkyl-3-methylimidazolidin-4-ones, prepared from arylmethyl-substituted α-amino acids, and a series of trans- and cis-2-(fluoromethyl)-2,3-dimethylimidazolidin-4-ones, derived from L-valine and L-leucine, were synthesized and fully characterized. Their catalytic activity was evaluated in the addition of 1-methylindole to cinnamaldehyde. Using the cis-5-arylmethyl-2-alkyl-3-methylimidazolidin-4-one catalysts, enantioselectivities of up to 78% ee (S) were achieved. Notably, with the L-valine-derived cis-imidazolidinone organocatalyst, the highest reversal of stereoselectivity to date (92% ee, (R) at –43 °C) was observed.

• Language: English
• Keywords: asymmetric organocatalysis, imidazolidinone organocatalysts, iminium ion organocataly-sis, reversal of stereoselectivity, enantioselectivity, self-regeneration of stereocenters (SRS)
• 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: 2026
• Number of pages: 34 str.
• Numbering: Vol. 31, iss. 15, art. 2684
• PID: 20.500.12556/RUL-185480
• UDC: 547.78
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules31152684
• COBISS.SI-ID: 287150083
• Publication date in RUL: 06.08.2026

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

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: asimetrična organokataliza, organokatalizatorji na osnovi imidazolidinona, iminijeva organokataliza, obrnitev stereoselektivnosti, enantioselektivnost, samoregeneracija stereogenega centra (SRS)

Projects

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

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: I0-0022-2022
• Name: Mreža raziskovalnih infrastrukturnih centrov Univerze v Ljubljani (MRIC UL)