1620143-03-4Relevant academic research and scientific papers
Metal-free intermolecular cyclopropanation between alkenes and iodonium ylides mediated by PhI(OAc)2·Bu4NI
Tao, Jason,Estrada, Carl D.,Murphy, Graham K.
supporting information, p. 9004 - 9007 (2017/08/15)
A rapid, mild and metal-free intermolecular cyclopropanation between iodonium ylides and alkene-containing substrates mediated by PhI(OAc)2·Bu4NI is reported. Iodonium ylides of cyclic and acyclic 1,3-dicarbonyls were reacted with a variety of mono-, di-, tri- and tetra-substituted alkenes of various structural types to give 29 cyclopropanes in up to 97% yield.
Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B
Nambu, Hisanori,Ono, Naoki,Yakura, Takayuki
, p. 1892 - 1901 (2016/06/15)
Acid-catalyzed ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes under metal-free conditions proceeded smoothly at room temperature to provide 2-aryl-3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in excellent yields without the formation
An efficient synthesis of cycloalkane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using (1-aryl-2-bromoethyl)-dimethylsulfonium bromides: Application to a one-pot synthesis of tetrahydroindol-4(5H)-one
Nambu, Hisanori,Fukumoto, Masahiro,Hirota, Wataru,Ono, Naoki,Yakura, Takayuki
supporting information, p. 4312 - 4315 (2015/06/22)
An efficient synthesis of cyclohexane- and cyclopentane-1,3-dione-2-spirocyclopropanes from 1,3-cycloalkanediones using sulfonium salts was achieved. The reaction of 1,3-cycloalkanediones with (1-aryl-2-bromoethyl)-dimethylsulfonium bromides and powdered K2CO3 in EtOAc provided the corresponding spirocyclopropanes in high yields. Furthermore, a one-pot synthesis of tetrahydroindol-4(5H)-one from 1,3-cyclohexanedione was achieved using the present protocol and a sequential ring-opening cyclization of spirocyclopropane with a primary amine.
Metal-catalyzed thermal reactions of cyclic β-Dicarbonyl Phenyliodonium Ylide with Styrenes
Bosnidou, Alexandra-Eleni,Kalpogiannaki, Dimitra,Karanestora, Sofia,Nixas, John A.,Hadjiarapoglou, Lazaros P.
, p. 1279 - 1283 (2015/01/30)
A cyclic β-dicarbonyl phenyliodonium ylide reacted with various substituted styrenes under Rh2(OAc)4 catalysis to give cyclopropanes and dihydrofurans in a highly regioselective fashion. When styrenes with electron-donating substituents or disubstituted were employed, only dihydrofurans were isolated instead. A mechanism involving two competing pathways rationalizes the results.
Ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with amines: Rapid access to 2-substituted 4-hydroxyindole
Nambu, Hisanori,Fukumoto, Masahiro,Hirota, Wataru,Yakura, Takayuki
supporting information, p. 4012 - 4015 (2014/08/18)
An efficient ring-opening cyclization of cyclohexane-1,3-dione-2- spirocyclopropanes with primary amines has been developed. The reaction proceeded at room temperature without any additives to provide 2-substituted tetrahydroindol-4-ones in good to excellent yields without the formation of the 3-substituted isomers. The obtained product was readily converted into a 2-substituted 4-hydroxyindole derivative via a synthetically useful indoline intermediate.
