Synthesis and organocatalytic activity of imidazolidinone organocatalystsPetek, Nejc (Avtor) Ciber, Luka (Avtor) Golobič, Amalija (Avtor) Mihevc, Andrej (Avtor) Požgan, Franc (Avtor) Svete, Jurij (Avtor) Štefane, Bogdan (Avtor) Grošelj, Uroš (Avtor) asymmetric organocatalysisimidazolidinone organocatalystsiminium ion organocataly-sisreversal of stereoselectivityenantioselectivityself-regeneration of stereocenters (SRS) 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.20262026-08-06 13:49:21Članek v reviji185480UDK: 547.78ISSN pri članku: 1420-3049DOI: 10.3390/molecules31152684COBISS_ID: 287150083sl