Hydrogen-Bonding Ability of Noyori–Ikariya Catalysts Enables Stereoselective Access to CF(3)-Substituted syn-1,2-Diols via Dynamic Kinetic Resolution

[Image: see text] 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. Th...

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Detalles Bibliográficos
Autores principales: Sterle, Maša, Huš, Matej, Lozinšek, Matic, Zega, Anamarija, Cotman, Andrej Emanuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167654/
https://www.ncbi.nlm.nih.gov/pubmed/37180962
http://dx.doi.org/10.1021/acscatal.3c00980
Descripción
Sumario:[Image: see text] 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.

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