Magnetically recoverable catalyst for the asymmetric Henry reaction based on a substituted imidazolidine-4-one copper(II) complex supported by Fe3O4·SiO2 nanoparticles

• Published in: Tetrahedron: asymmetry 2015-12, Vol.26 (21-22), p.1300-1306
• Main Authors: Bhosale, Dattatry Shivajirao, Drabina, Pavel, Kincl, Miloslav, Vlček, Milan, Sedlák, Miloš
• Format: Article
• Language: English
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/j.tetasy.2015.10.003

[Display omitted] The preparation and characterization of a heterogeneous recyclable catalyst based on Cu(II) complex of magnetic nanoparticles Fe3O4·SiO2 with (2R,5S)-5-isopropyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one is described. The ligand molecules were attached to the surface by means of coordination bonds. The catalyst was characterized using DLS, FT-IR spectroscopy, SEM, and microanalysis. The reaction of substituted aldehydes with nitromethane catalyzed with this complex proceeded with high yields (82–99%) and high enantioselectivity (68–94%). The reaction rate decreased due to the formation of aggregated forms of the catalyst nanoparticles whose size (115–834nm) depends on their concentration in the reaction medium. After a tenfold recycling of the catalyst, the catalytic activity slightly decreased (∼10%); however, no change in enantioselectivity was observed (∼94% ee). The efficiency of the catalyst prepared was also verified in the preparation of an intermediate of synthesis of the medical drug (R)-Salmeterol (yield 72%; 91% ee).