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

Submitting author affiliation:
University of Pardubice, Pardubice, Czech Republic

Beilstein Arch. 2023, 202361. https://doi.org/10.3762/bxiv.2023.61.v1

Published 14 Dec 2023

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Abstract

The new chiral ligands I-III based on derivatives of imidazolidine-4-one were synthesised and characterised. The catalytic activity and enantioselectivity of their corresponding copper(II) complexes were studied in the asymmetric Henry reaction. It was found out that the enantioselectivity of these catalysts is very high overall 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 reaction. Under optimised reaction conditions, aldol products with enantioselectivity of up to 91 % ee were obtained.

Keywords: Asymmetric Henry reaction; Asymmetric aldol reaction; Chiral ligands; Enantioselective catalysis; Imidazolidine derivatives

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Bartáček, J.; Chlumský, K.; Mrkvička, J.; Paloušová, L.; Sedlák, M.; Drabina, P. Beilstein Arch. 2023, 202361. doi:10.3762/bxiv.2023.61.v1

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