97023-74-0Relevant articles and documents
Cyclopentane Formation from Flexible Precursors Using Samarium(II) Reagents
Aretz, Christopher D.,Escobedo, Humberto,Cowen, Bryan J.
, p. 1880 - 1884 (2018/05/09)
Three efficient methods for five-membered ring carbocycle synthesis have been developed from simple starting materials using samarium(II) reagents. A Reformatsky aldol reaction proceeded efficiently with samarium(II) iodide using lithium bromide as an additive. A new intramolecular alkylation of a samarium enolate was realized with a pendant sulfonate ester leaving group. Pinacol cyclization of a simple diketone was also demonstrated giving a diol product in high stereoselectivity. A promising lead result has been established demonstrating enantioselectivity in a chiral ligand controlled Reformatsky aldol reaction.
Chemospecificity in arylations of δ- and γ-ketocarboxylic acids with P2O5-MsOH, TfOH, and related acidic media
Yonezawa, Noriyuki,Koike, Masayuki,Kameda, Asami,Naito, Shin,Hino, Tetsuo,Maeyama, Katsuya,Ikeda, Tomiki
, p. 3169 - 3180 (2007/10/03)
Remarkable contrast between chemospecificities in acid-mediated arylation of δ- and γ-ketocarboxylic acids was revealed: in the presence of P2O5-MsOH, TfOH, PPA, and MsOH, arylation of δ-ketocarboxylic acid 1A with arenes takes place
Synthesis and Application of Imidazole Derivatives: Preparation of Various Diketones from 1,n-Bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-diones
Hayakawa, Satoshi,Baba, Junko,Okamoto, Masao,Ohta, Shunsaku
, p. 22 - 32 (2007/10/02)
Reaction of 1,n-bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-dione (8) with an excess of Grignard reagent was examined.In the cases of n = 4 and 5, precursors (14) for synthesis of various asymmtric 1,4- and 1,5-diketones (12: R1 R2), respectively, were obtained in good yields by treating 8 with an excess of methylmagnesium iodide in ether followed by trimethylsilylation.In the case of n >/= 8, the two carbonyl groups of 8 were both attacked by the Grignard reagent, and the products (11: R1=R2=CH3) were convertible to symmetrical diketones (12: R1=R2=CH3) in good yields.In cases of n = 6 and 7, the mode of the Grignard reaction was transitional between the two types.Keywords - 2-acyl-1H-imidazole; 1,n-bis(1-methyl-1H-imidazol-2-yl)-1,n-alkanedione; diketone synthesis; asymmetric diketone; symmetric diketone; Grignard reaction; dihydrojasmone; cis-jasmone; muscone; 2-(1-hydroxy-1-alkyl)-1-methyl-1H-imidazole