An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes.
Reflecting the importance of fluorinated organic compounds in medicinal chemistry, development of an efficient method for catalytic enantioselective fluorination is increasingly desirable. Using a novel palladium complex 2 (1-2.5 mol %), various beta-ketoesters including cyclic and acyclic substrates were fluorinated with excellent enantioselectivity in the range of 83-94% ee. It is environmentally advantageous that this reaction proceeds well in solvents such as EtOH, rather than usual organic solvents. Furthermore, the product was successfully tranformed into both alpha-fluoro beta-hydroxy and beta-amino acid derivatives, which should be extremely useful in developing novel drugs.
Hamashima
Yoshitaka
Y
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Katahira, Sendai, Miyagi 980-8577, Japan.
Yagi
Kenji
K
Takano
Hisashi
H
Tamás
László
L
Sodeoka
Mikiko
M
D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D009942:Organometallic Compounds; D010165:Palladium