Hydrogen-bonding ability of Noyori–Ikariya catalysts enables stereoselective access to CF$_3$-substituted syn-1,2-diols via dynamic kinetic resolution
| Autor: | Maša Sterle, Matej Huš, Matic Lozinšek, Anamarija Zega, Andrej Emanuel Cotman |
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| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: |
ketones
rutenij drug design asymmetric catalysis General Chemistry stereoselectivity DFT Catalysis catalysts asimetrična kataliza oblikovanje zdravil kemijska kinetika udc:544.4 hidrogenacija noncovalent interactions fluorine redox reactions fluor kinetic resolution hydrogenation ruthenium kinetična ločljivost |
| Zdroj: | ACS catalysis, vol. 13, no. 9, pp. 6242-6248, 2023. |
| ISSN: | 2155-5435 |
| Popis: | Stereopure CF$_3$-substituted syn-1,2-diols were prepared via the reductive dynamic kinetic resolution of the corresponding racemic α-hydroxyketones in HCO$_2$H/Et$_3$N. (Het)aryl, benzyl, vinyl, and alkyl ketones are tolerated, delivering products with ≥95% ee and ≥87:13 syn/anti. This methodology offers rapid access to stereopure bioactive molecules. Furthermore, DFT calculations for three types of Noyori–Ikariya ruthenium catalysts were performed to show their general ability of directing stereoselectivity via the hydrogen bond acceptor SO$_2$ region and CH/π interactions. |
| Databáze: | OpenAIRE |
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