title: Diastereoselective Johnson-Corey-Chaykovsky trifluoroethylidenation.
abstract: (2,2,2-Trifluoroethyl)diphenylsulfonium triflate was found to be an efficient ylide reagent for the Johnson-Corey-Chaykovsky reaction to afford trifluoromethyl epoxides, cyclopropanes and aziridines. Interestingly, excellent but different diastereoselectivity was observed for these transformations. Both trifluoromethyl epoxides and cyclopropanes were obtained with trans-selectivity, whereas aziridines were obtained with cis-selectivity.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. jchxiao@sioc.ac.cn.
authors.forename: Yaya
authors.initials: Y
authors.lastname: Duan
authors.forename: Bin
authors.initials: B
authors.lastname: Zhou
authors.forename: Jin-Hong
authors.initials: JH
authors.lastname: Lin
authors.forename: Ji-Chang
authors.initials: JC
authors.lastname: Xiao
mesh_terms: D001388:Aziridines / Q000737:chemistry; D003521:Cyclopropanes / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D003521:Cyclopropanes; D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated