Catalytic enantioselective fluorination of oxindoles.
We have developed a highly efficient catalytic enantioselective fluorination of oxindole derivatives. In the presence of a catalytic amount of chiral Pd complex 2 (2.5 mol %), various substrates, including aryl- and alkyl-substituted oxindoles, were fluorinated in a highly enantioselective manner (up to 96% ee). In addition, when R was a hydrogen atom, enantioselective fluorination followed by solvolysis gave a monofluorinated ester with up to 93% ee. To our knowledge, this is the first example of catalytic enantioselective fluorination of oxindoles.
Hamashima
Yoshitaka
Y
Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Miyagi, 980-8577, Japan.
Suzuki
Toshiaki
T
Takano
Hisashi
H
Shimura
Yuta
Y
Sodeoka
Mikiko
M
D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D010648:Phenylacetates / Q000138:chemical synthesis; D013237:Stereoisomerism
D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D010648:Phenylacetates; D010165:Palladium