Stereoselective Iridium-N,P-Catalyzed Double Hydrogenation of Conjugated Enones to Saturated Alcohols.

ABSTRACT: Asymmetric hydrogenation of prochiral substrates such as ketones and olefins constitutes an important instrument for the construction of stereogenic centers, and a multitude of catalytic systems have been developed for this purpose. However, due to the different nature of the π-system, the hydrogenation of olefins and ketones is normally catalyzed by different metal complexes. Herein, a study on the effect of additives on the Ir-N,P-catalyzed hydrogenation of enones is described. The combination of benzamide and the development of a reactive catalyst unlocked a novel reactivity mode of Crabtree-type complexes toward C═O bond hydrogenation. The role of benzamide is suggested to extend the lifetime of the dihydridic iridium intermediate, which is prone to undergo irreversible trimerization,

SUBMITTER: Peters BBC 

PROVIDER: S-EPMC9121388 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature