Iridium-Catalyzed Regio- and Enantioselective Hydrogenation of 5‑Alkylidene Cyclopentenones.

ABSTRACT: The regio- and enantioselective hydrogenation of the CC bond in molecules with two or more CC bonds of the same type is very challenging but highly desirable. Herein, we report a regio- and enantioselective hydrogenation of 5-alkylidene cyclopentenones catalyzed by an Ir/BiphPHOX complex, delivering the corresponding mono- and double-hydrogenated products in excellent results, respectively (5-substituted cyclopentenones: up to 99% yield and 98% ee; 2,4-disubstituted cyclopentanones: up to 99% yield, 16:1 dr, and 99% ee). For the chiral 2,4-disubstituted cyclopentanones, the results of mechanistic studies indicated that both the exo- and endocyclic CC bonds of the substrate can be preferentially reduced with the exocyclic CC bond undergoing hydrogenation more readily. The ester group in

SUBMITTER: Wei H 

PROVIDER: S-EPMC12933482 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature