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Hydrogen-bonding ability of Noyori–Ikariya catalysts enables stereoselective access to CF$_3$-substituted syn-1,2-diols via dynamic kinetic resolution
- Source :
- ACS catalysis, vol. 13, no. 9, pp. 6242-6248, 2023.
- Publication Year :
- 2023
- Publisher :
- American Chemical Society, 2023.
-
Abstract
- 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.
- Subjects :
- 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
Subjects
Details
- Language :
- English
- ISSN :
- 21555435
- Database :
- OpenAIRE
- Journal :
- ACS catalysis, vol. 13, no. 9, pp. 6242-6248, 2023.
- Accession number :
- edsair.doi.dedup.....ffb53ef41cc7bd3f529a02e6323ed2b3