title: Reagent-Controlled Tandem Reactions of Vinyl Epoxides: Access to Functionalized γ-Butenolides.
abstract: A new approach to functionalized γ-butenolides based on reagent-controlled tandem reaction sequences of Morita-Baylis-Hillman-type vinyl epoxides is described. The nucleophilic addition of a tertiary phosphine to the electron-deficient alkene led to ring-opening of the epoxide followed by lactonization to produce phosphonium ylides, which could undergo Wittig olefination with aryl trifluoromethyl ketones and aryl aldehydes to give 3-alkenyl γ-butenolides in moderate to good yields and high E/Z selectivity. Tertiary amine promoted the Michael-type addition of carbon- and nitrogen-based nucleophiles to the vinyl epoxides followed by lactonization to provide diverse 3-substituted γ-butenolides.
authors.affiliation: Department of Pharmaceutical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, P. R. China.
authors.forename: Juan
authors.initials: J
authors.lastname: Ma
authors.affiliation: Department of Pharmaceutical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, P. R. China.
authors.forename: Zhe-zhe
authors.initials: ZZ
authors.lastname: Yuan
authors.affiliation: Department of Pharmaceutical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, P. R. China.
authors.forename: Xiang-wen
authors.initials: XW
authors.lastname: Kong
authors.affiliation: Department of Pharmaceutical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, P. R. China.
authors.forename: Huai
authors.initials: H
authors.lastname: Wang
authors.affiliation: Department of Pharmaceutical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, P. R. China.
authors.forename: Yi-ming
authors.initials: YM
authors.lastname: Li
authors.affiliation: Department of Pharmaceutical Engineering, Hefei University of Technology , 193 Tunxi Road, Hefei 230009, P. R. China.|Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, P. R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Xiao
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, P. R. China.
authors.forename: Gang
authors.initials: G
authors.lastname: Zhao