Synthesis of chiral α-fluoroketones through catalytic enantioselective decarboxylation

Abstract

(Chemical Equation Presented) 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. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.