Hydrogen-Bonding Ability of Noyori-Ikariya Catalysts Enables Stereoselective Access to CF₃-Substituted syn-1,2-Diols via Dynamic Kinetic Resolution.

ABSTRACT: Stereopure CF₃-substituted syn-1,2-diols were prepared via the reductive dynamic kinetic resolution of the corresponding racemic α-hydroxyketones in HCO₂H/Et₃N. (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 SO₂ region and CH/π interactions.

SUBMITTER: Sterle M 

PROVIDER: S-EPMC10167654 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature