Recyclable catalyst for the asymmetric Henry reaction based on functionalized imidazolidine-4-one-copper(II) complexes supported by a polystyrene copolymer

• Published in: Tetrahedron letters Vol. 56; no. 45; pp. 6240 - 6243
• Main Authors: Harmand, Lydie, Drabina, Pavel, Pejchal, Vladimír, Husáková, Lenka, Sedlák, Miloš
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.11.2015; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Henry reaction; Imidazolidine-4-one derivatives; Physical Sciences; Polystyrene; Recyclable enantioselective catalyst; Science & Technology; Imidazolidine-4-one derivatives; Polystyrene; Recyclable enantioselective catalyst; Henry reaction; COPPER(II) COMPLEXES; LIGANDS; RESINS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.09.112

[Display omitted] Imidazolidine-4-one derivatives were anchored by the thiol-ene click reaction to a swellable pearl-like polystyrene copolymer and their complexes with Cu(II) acetate were utilized as recyclable heterogeneous catalysts for the Henry reaction of substituted aldehydes with nitromethane. The corresponding 2-nitroethanols were mostly obtained in high yields (65–99%) and with enantioselectivities of up to 92% ee. After a fivefold recycling of the catalyst, the decrease in enantioselectivity was negligible (Δ 3% ee).