Kőszegi Kristóf András and Szabados Márton and Szőllősi György: Mechanochemically assisted, environmentally benign heterogeneous Asymmetric Michael addition to maleimides.
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Abstract
Chiral N-substituted succinimides are widely used intermediates in the pharmaceutical industry. The Michael additions of various nucleophiles to maleimides results in such compounds. In the industry, since the upraise of environmental awareness, there is a huge demand of sustainable synthetic methods. Therefore, efficient alternative reaction activations are highly examined. Asymmetric catalytic processes have been developed for Michael additions to maleimides under batch conditions using organocatalysts. Our aim was to implement mechanochemical activation in these reactions because of its huge benefits over the conventional methods, i.e. the possibility of applying solvent-free conditions and the significantly reduced reaction times. We set the goal to prepare N-substituted succinimides with high yields and enantioselectivity using isobutyraldehyde as nucleophile and L-phenylalanine adsorbed on the surface of inorganic oxides (Bentolite H and Laponite RD) as heterogeneous organocatalyst. N-methylmaleimide as reactant was used to optimise the reaction and milling parameters. We also studied the structure of the catalyst using different methods to examine the deposition of L-Phe on the inorganic oxide. As a result of our studies, optimal conditions were determined to carry out the preparation of various N-substituted succinimides, which may be a significant step in the development of sustainable industrial synthetic methods.
| Item Type: | Conference or Workshop Item |
|---|---|
| Journal or Publication Title: | Proceedings of the International Symposium on Analytical and Environmental Problems |
| Date: | 2024 |
| Volume: | 30 |
| ISBN: | 978-963-688-009-5 |
| Page Range: | pp. 313-317 |
| Language: | English |
| Publisher: | University of Szeged |
| Place of Publication: | Szeged |
| Event Title: | 30th International Symposium on Analytical and Environmental Problems |
| Event Type: | Conference |
| Event Location: | Szeged |
| Event Dates: | 2024. október 7-8. |
| Related URLs: | https://acta.bibl.u-szeged.hu/85607/ |
| Uncontrolled Keywords: | Környezetkémia, Katalízis |
| Additional Information: | Bibliogr.: 317. p. ; ill. |
| Subjects: | 01. Natural sciences 01. Natural sciences > 01.04. Chemical sciences |
| Date Deposited: | 2024. Nov. 26. 13:22 |
| Last Modified: | 2024. Nov. 26. 13:22 |
| URI: | http://acta.bibl.u-szeged.hu/id/eprint/85747 |
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