2008/02/16 by Zengming Shen, Hasan Khan, Vy M. Dong · 1 citation
Chemistry · #Catalytic C–H Functionalization Methods #Asymmetric Hydrogenation and Catalysis #Synthetic Organic Chemistry Methods
paper · doi:10.1021/ja7109025
openalex publication_date 2008/02/16 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26
This communication describes the design and execution of a novel approach to forming chiral lactones via C−H bond activation. The strategy features an unprecedented enantioselective Rh-catalyzed hydroacylation of carbon−oxygen double bonds. Representative keto-aldehydes (derived from salicylaldehyde) undergo cyclization with complete regioselectivity to afford seven-membered lactones in great enantiomeric excess (≥99% ee). The basicity of the phosphine ligand is shown to play a critical role in promoting hydroacylation over competitive decarbonylation.