Hydrogen-bonding ability of Noyori–Ikariya catalysts enables stereoselective access to CF$_3$-substituted syn-1,2-diols via dynamic kinetic resolution

Sterle, Maša (author), Huš, Matej (author), Lozinšek, Matic (author), Zega, Anamarija (author), Cotman, Andrej Emanuel (author)

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.

• Language: English
• Keywords: asymmetric catalysis, DFT, drug design, fluorine, hydrogenation, kinetic resolution, ruthenium, catalysts, ketones, noncovalent interactions, redox reactions, stereoselectivity
• Work type: Article
• Typology: 1.03 - Short Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2023
• Number of pages: Str. 6242-6248
• Numbering: Vol. 13, iss. 9
• PID: 20.500.12556/RUL-147228
• UDC: 544.4
• ISSN on article: 2155-5435
• DOI: 10.1021/acscatal.3c00980
• COBISS.SI-ID: 150693379
• Publication date in RUL: 27.06.2023

Record is a part of a journal

• Title: ACS catalysis
• Shortened title: ACS catal.
• Publisher: American Chemical Society
• ISSN: 2155-5435
• COBISS.SI-ID: 518529817

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

• Language: Slovenian
• Keywords: asimetrična kataliza, oblikovanje zdravil, fluor, hidrogenacija, kinetična ločljivost, rutenij, kemijska kinetika