Natural chiral catalysts on solid surfaces used in Michael addition to maleimides
As the most important molecules in living organisms are chiral, the selective production of the optical isomers of substances designed to interact with them, such as drugs, is of paramount importance. In addition, from an environmental point of view, it is also desirable to carry out the asymmetric...
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| Dokumentumtípus: | Könyv része |
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University of Szeged
Szeged
2021
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| Sorozat: | Proceedings of the International Symposium on Analytical and Environmental Problems
27 |
| Kulcsszavak: | Analitikai kémia, Gyógyszerkémia |
| Tárgyszavak: | |
| Online Access: | http://acta.bibl.u-szeged.hu/75963 |
| Tartalmi kivonat: | As the most important molecules in living organisms are chiral, the selective production of the optical isomers of substances designed to interact with them, such as drugs, is of paramount importance. In addition, from an environmental point of view, it is also desirable to carry out the asymmetric syntheses as efficiently as possible, thus minimising waste production. Asymmetric catalytic syntheses are one of the best methods for producing enantiomerically pure compounds, whereby the heterogenization of the chiral catalysts can allow their reuse. A simple method to heterogenize chiral catalysts is the adsorption of optically pure material on a solid surface. Some examples of the use of heterogeneous chiral catalysts that can be readily prepared by adsorption are known, however, solids of this type have not yet been used in reactions of maleimides. Based on these, we set out to explore the combined catalytic effect of natural amino acids and various inorganic oxides in Michael additions between maleimides and aldehydes. The investigation of a variety of starting materials provides an opportunity to study the activity, stereoselectivity and the applicability of these simple chiral catalysts. Our studies have shown that while natural amino acids have only negligible catalytic activity, adsorption on different oxide surfaces (alumina, bentonite or laponite) gave succinimide derivatives with excellent conversions and enantioselectivities. In conclusion, our research has led to the development of a novel chiral heterogeneous catalytic system that can be used to produce valuable optically pure intermediates for use in the pharmaceutical industry. |
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| Terjedelem/Fizikai jellemzők: | 193-197 |
| ISBN: | 978-963-306-835-9 |