Heterogeneous asymmetric Michael additions using environmentally friendly catalysis : application of chiral inorganic-organic hybrid materials

Szőllősi, György and Kolcsár, Vanessza Judit and Kozma, Viktória and Fancsali, Brigitta and Mogyorós, Attila Zsolt and Gombkötő, Dániel and Kőhl, Gabriella: Heterogeneous asymmetric Michael additions using environmentally friendly catalysis : application of chiral inorganic-organic hybrid materials. In: Proceedings of the International Symposium on Analytical and Environmental Problems. pp. 409-413. (2019)

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Abstract

In the last few decades, the development of environmentally benign, sustainable processes for the preparation of optically pure intermediates used in the pharmaceutical, food and agrochemical industries received increasing attention. Processes applying recyclable, chiral heterogeneous catalysts based on readily available, natural, optically pure compounds may be convenient alternatives of the classical asymmetric synthetic methods. During our studies, we have attempted the development of novel heterogeneous catalysts by adsorption of natural amino acids on the surface of inorganic oxides. These materials formed either in-situ during reactions or prepared ex-situ were tested in various asymmetric Michael additions. Amino acids adsorbed on laponite were found the most efficient in catalyzing the addition of aldehydes or ketones to nitrostyrene derivatives. In these reactions occurring via enamine catalysis, the material obtained by adsorption of proline was found to be a highly active and stereoselective catalyst, although proline afforded low enantioselectivities. In the Michael addition of nitroalkanes or β-keto esters to unsaturated ketones, both laponite and alumina were efficient in increasing the enantioselectivities. In these reactions, which take place through iminium catalysis, only moderate enantioselectivities could be reached. The chiral inorganic-organic hybrid materials were characterized by infrared spectroscopy and powder X-ray diffractometry, evidencing bonding of the amino acids on the surface of the oxides. Our results demonstrated that an inorganic surface on which a chiral organocatalyst is immobilized by simple adsorption may have beneficial effect on the asymmetric reaction catalyzed by the chiral material, due to surface improved asymmetric induction. In conclusion, these hybrid materials are promising candidates for future application in environmentally friendly processes.

Item Type: Article
Journal or Publication Title: Proceedings of the International Symposium on Analytical and Environmental Problems
Date: 2019
ISBN: 978-963-306-702-4
Page Range: pp. 409-413
Event Title: International Symposium on Analytical and Environmental Problems (25.) (2019) (Szeged)
Uncontrolled Keywords: Sztereokémia, Szerves kémia
Additional Information: Bibliogr.: 413. p. ; összefoglalás angol nyelven
Date Deposited: 2020. Mar. 23. 09:51
Last Modified: 2020. Mar. 23. 09:51
URI: http://acta.bibl.u-szeged.hu/id/eprint/64894

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