Selective Synthesis of Chiral Carbocycles by Iridium-Catalyzed Asymmetric Mono-, Double-, or Triple Hydrogenation of Cyclic Dienones.

ABSTRACT: A divergent N,P-iridium-catalyzed asymmetric hydrogenation of cyclic dienones into chiral cyclohexenones, cyclohexanones, or cyclohexanols is described. The π-bonds in cyclic dienones underwent hydrogenation in a sequential manner, favoring the (s)-cis conformed alkene followed by the olefin in the (s)-trans conformation and at last the ketone, to install up to three stereocenters in a single step. The simple choice of the proper catalyst allowed the formation of each respective product in high yield and stereopurity (up to 99% ee, up to 99/1 d.r.). This protocol provides an interesting opportunity to access multiple and stereopure carbocycles starting from the same precursor that otherwise require multistep syntheses.

SUBMITTER: Peters BBC 

PROVIDER: S-EPMC12797332 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature