title: Stereoselective synthesis of 3-methyleneisoindolin-1-ones via base-catalyzed intermolecular reactions of electron-deficient alkynes with N-hydroxyphthalimides.
abstract: Highly stereoselective intermolecular reactions of electron-deficient alkynes with N-hydroxyphthalimides for efficient construction of N-unprotected 3-methyleneisoindolin-1-ones have been developed through base catalytic strategies. The reaction of alkynoates with N-hydroxyphthalimides catalyzed by Bu3P in DMF at 150 °C gave the corresponding 3-methyleneisoindolin-1-ones with a (Z)-configuration, while the reaction of alkynoates with N-hydroxyphthalimides catalyzed by K2CO3 in DMF at 60 °C gave the corresponding 3-methyleneisoindolin-1-ones with an (E)-configuration, and (Z)-3-methyleneisoindolin-1-ones were obtained when alkyne ketones reacted with N-hydroxyphthalimide.
authors.affiliation: †School of Basic Sciences, China Pharmaceutical University, Nanjing, 210009, P. R. China.
authors.forename: Xin
authors.initials: X
authors.lastname: Chen
authors.affiliation: †School of Basic Sciences, China Pharmaceutical University, Nanjing, 210009, P. R. China.
authors.forename: Fei-Fei
authors.initials: FF
authors.lastname: Ge
authors.affiliation: †School of Basic Sciences, China Pharmaceutical University, Nanjing, 210009, P. R. China.
authors.forename: Tao
authors.initials: T
authors.lastname: Lu
authors.affiliation: †School of Basic Sciences, China Pharmaceutical University, Nanjing, 210009, P. R. China.|‡State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 210009, P. R. China.
authors.forename: Qing-Fa
authors.initials: QF
authors.lastname: Zhou
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D054833:Isoindoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010755:Organophosphates / Q000737:chemistry*; D010797:Phthalimides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000591957:3-methyleneisoindolin-1-one; D000480:Alkynes; D054833:Isoindoles; D010755:Organophosphates; D010797:Phthalimides; C009524:tributyl phosphate; C037437:N-hydroxyphthalimide