Synthesis of Chiral α-Fluoroketones through Catalytic Enantioselective Decarboxylation


  • This work was supported in part by the Japan Science and Technology Agency (JST) and the Ministry of Education, Culture, Sports, Science, and Technology of Japan through a Grant-in-Aid for Exploratory Research and for the 21st Century COE Program for Frontiers in Fundamental Chemistry. A.H. is grateful to the Japan Society for the Promotion of Science for a postdoctoral fellowship.


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A conceptually new approach affords optically active α-fluoroketones 3 in high yields with up to 99 % ee from racemic α-fluoro-β-ketoesters 1 in the presence of a chiral phosphinooxazoline ligand 2. The palladium-catalyzed decarboxylation/allylation reaction also allows the highly enantioselective construction of an all-carbon quaternary center. dba=dibenzylideneacetone.