title: Tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic: stereoselective nucleophilic difluoromethylation of aryl ketones.
abstract: A stereoselective synthesis of enantiomerically enriched difluoromethyl tertiary alcohols by tuning the reactivity of difluoromethyl sulfoximines from electrophilic to nucleophilic difluoromethylating agents is reported. The key feature of this chemistry is the diastereoselective addition of the difluoromethyl sulfoximine to the prochiral carbon of the ketone. The present method was used to prepare enantiomerically enriched difluoromethyl secondary alcohols and difluorinated analogues of the natural products gossonorol and boivinian B, demonstrating the potency of the method.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling-Ling Road, Shanghai 200032, P. R. China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Shen
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.forename: Chuanfa
authors.initials: C
authors.lastname: Ni
authors.forename: Yucheng
authors.initials: Y
authors.lastname: Gu
authors.forename: Jinbo
authors.initials: J
authors.lastname: Hu
mesh_terms: D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006845:Hydrocarbons, Fluorinated; D007097:Imines; D007659:Ketones