title: Catalytic enantioselective fluorination of oxindoles.
abstract: 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.
authors: Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Miyagi, 980-8577, Japan.
authors: Yoshitaka
authors: Y
authors: Hamashima
authors: Toshiaki
authors: T
authors: Suzuki
authors: Hisashi
authors: H
authors: Takano
authors: Yuta
authors: Y
authors: Shimura
authors: Mikiko
authors: M
authors: Sodeoka
mesh_terms: D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D010648:Phenylacetates / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D010648:Phenylacetates; D010165:Palladium