title: Synthesis of pentafluorinated β-hydroxy ketones.
abstract: The LHMDS-promoted in situ generation of difluoroenolates from readily available 1-aryl and 1-alkyl 2,2,4,4,4-pentafluorobutan-1,3-dione hydrates has been used to produce a series of pentafluorinated β-hydroxy ketones in up to 95% yield. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and is complete within 10 min. Reduction toward the corresponding 1,3-diol with DIBAL gives quantitative amounts and favors the formation of the syn-isomer.
authors.affiliation: Department of Chemistry, Georgetown University, Washington, DC 20057, United States.
authors.forename: Peng
authors.initials: P
authors.lastname: Zhang
authors.forename: Christian
authors.initials: C
authors.lastname: Wolf
mesh_terms: D002074:Butanones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002074:Butanones; D006845:Hydrocarbons, Fluorinated; D007659:Ketones