title: Highly enantioselective monofluoromethylation of C2-arylindoles using FBSM under chiral phase-transfer catalysis.
abstract: The highly enantioselective addition of 1-fluoro-1,1-bis(phenylsulfonyl)methane (FBSM) to vinylogous imines generated in situ from 2-aryl-3-(1-arylsulfonylmethyl)indoles was achieved using chiral ammonium salts derived from cinchona alkaloids. One-pot conversion from 2-arylindoles with FBSM was also adaptable under the same reaction conditions. The key for this transformation is the effective use of the arylsulfonyl group.
authors.affiliation: Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Matsuzaki
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Furukawa
authors.forename: Etsuko
authors.initials: E
authors.lastname: Tokunaga
authors.forename: Takashi
authors.initials: T
authors.lastname: Matsumoto
authors.forename: Motoo
authors.initials: M
authors.lastname: Shiro
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
mesh_terms: D064751:Ammonium Compounds / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D044367:Phase Transition; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: C585254:1-fluoro-1,1-bis(phenylsulfonyl)methane; D064751:Ammonium Compounds; D002930:Cinchona Alkaloids; D007211:Indoles; D013438:Sulfhydryl Compounds