title: Chemoselective synthesis of trifluoromethylated γ-butenolide derivatives via phosphine-promoted tandem reaction of allylic carbonates and trifluoromethyl ketones.
abstract: A novel chemoselective phosphine-mediated tandem reaction between nonsubstituted MBH carbonates and aryl trifluoromethyl ketones is described. The product selectivity of the reaction is easily tunable by changing the ratios of the two reactants, and mono- or bicyclic bistrifluoromethylated vinyl γ-butenolide products can be prepared with good chemoselectivity in modest-to-good yields and diastereoselectivities. The formation of the bicyclic γ-butenolide structures via a one-pot four-step sequence under phosphine catalysis is unprecedented.
authors.affiliation: School of Medical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, China.
authors.forename: Hua
authors.initials: H
authors.lastname: Xiao
authors.forename: Hong-yu
authors.initials: HY
authors.lastname: Duan
authors.forename: Jun
authors.initials: J
authors.lastname: Ye
authors.forename: Ri-sheng
authors.initials: RS
authors.lastname: Yao
authors.forename: Juan
authors.initials: J
authors.lastname: Ma
authors.forename: Zhe-zhe
authors.initials: ZZ
authors.lastname: Yuan
authors.forename: Gang
authors.initials: G
authors.lastname: Zhao
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002254:Carbonates; D006845:Hydrocarbons, Fluorinated; D007659:Ketones; D010720:Phosphines; C004511:butenolide; C044646:phosphine; D015107:4-Butyrolactone