Asymmetric Electrophilic Fluorination of β-Keto Phosphonates in Ionic Liquid Media Catalyzed by Chiral Palladium Complexes Sung Min Kim, Young Ku Kang, Kil Sung Lee,

The chemistry of bioactive organofluorine compounds is a rapidly developing area of research because of their impor-tance in biochemical and medicinal application. 1 Chiral organofluorine compounds containing a fluorine atom bonded directly to a stereogenic center have been utilized in studies of enzyme mechanisms and as intermediates in asymmetric syntheses. 2 The development of effective methodologies for the preparation of new selectively fluorinated, stereochemically defined compounds is critical to further advances of fluorine chemistry. 3 The catalytic enantioselective construction of fluorinated stereogenic centers is still important challenge in modern organic chemistry. 4 α-Fluoroalkylphosphonates are better mimics of natural phosphates with matched 2nd pKa vaules (~6.5). 5 The enantioselective construction of α-fluoroalkylphosphonates is extremely important because the stereochemistry of α-carbon does affect enzyme binding. 6 Although there have been several reports for the asymmetric synthesis of α-fluoroalkylphosphonates, 7 synthetic methods of chiral α-fluoro β-keto phosphonates are limited. 8 The employment of ionic liquids as solvents for chemical reactions has been received increased attention because they have essentially no vapor pressure and provide high solubility for a wide range for organic and organometallic compounds. 9 These solvents are reusable, enhance the reactivity of chemical transformations, simplify product isolation and allow for catalysts recycling