Evaluation of the enantioselectivity of new chiral ligands based on imidazolidin-4-one derivatives

Autor: Jan Bartáček, Karel Chlumský, Jan Mrkvička, Lucie Paloušová, Miloš Sedlák, Pavel Drabina
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 20, Iss 1, Pp 684-691 (2024)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.20.62
Popis: The new chiral ligands I–III based on derivatives of imidazolidin-4-one were synthesised and characterised. The catalytic activity and enantioselectivity of their corresponding copper(II) complexes were studied in asymmetric Henry reactions. It was found that the enantioselectivity of these catalysts is overall very high and depends on the relative configuration of the ligand used; cis-configuration of ligand affords the nitroaldols with major enantiomer S- (up to 97% ee), whereas the application of ligands with trans-configuration led to nitroaldols with major R-enantiomer (up to 96% ee). The “proline-type” ligand IV was also tested in asymmetric aldol reactions. Under the optimised reaction conditions, aldol products with enantioselectivities of up to 91% ee were obtained.
Databáze: Directory of Open Access Journals