7500-91-6Relevant articles and documents
Organic dye-catalyzed radical ring expansion reaction
Deguchi, Masato,Fujiya, Akitoshi,Yamaguchi, Eiji,Tada, Norihiro,Uno, Bunji,Itoh, Akichika
, p. 15825 - 15830 (2018/05/04)
Herein, we reported an attractive method for synthesizing medium-sized rings that are catalyzed by erythrosine B under fluorescent light irradiation. This synthetic approach featured mild conditions, a facile procedure, a broad substrate scope, and modera
Cyclizations of unsaturated CR(COX)2 radicals. Manganese(III) acetate oxidative cyclizations of unsaturated acetoacetates and atom-transfer cyclizations of unsaturated haloacetoacetates give the same radicals
Curran, Dennis P.,Morgan, Tina M.,Eric Schwartz,Snider, Barry B.,Dombroski, Mark A.
, p. 6607 - 6617 (2007/10/02)
Comparable regio- and stereochemical results were obtained when cyclizations of a series of 2-substituted 3-oxohept-6-enoate (or oct-7-enoate) esters (acetoacetates) were conducted by manganese(III) acetate oxidation or by iodine or bromine atom transfer
Asymmetric Alkylation of β-Keto Esters with Optically Active Sulfonium Salts
Umemura, Kazuyuki,Matsuyama,Haruo,Watanabe, Nobuko,Kobayashi, Michio,Kamigata, Nobumasa
, p. 2374 - 2383 (2007/10/02)
Alkylation of the cyclic β-keto ester2-(methoxycarbonyl)-1-indanone (2) with racemic alkylsulfonium salts 1a-h gave 2-alkylindanones 3 and 4 in 60-96percent yields.The relative reactivities of the alkyl substituents of aryldialkylsulfonium salts 1e and 1f were quite different from those in SN2 alkylations.Asymmetric induction occured upon alkylation of 2 with optically active sulfonium salts. (R)-2-Ethyl-2-(methoxycarbonyl)cyclohexanone (11) was obtained in up to 16percent ee by alkylation of the enolate ion of 2-(methoxycarbonyl)cyclohexanone (9) with optically active (R)-(+)-(p-chlorophenyl)ethylmethylsulfonium d-10-camphorsulfonate (1k).Alkylation of the enolate ion of 2 with sulfonium salts containing optically active alkyl groups afforded C-alkylated products with inversion of configuration at the asymmetric alkyl carbon atom.These alkylations appear to proceed via an S-O sulfurane intermediate or a tight ion pair with subsequent stereoselective alkyl migration to the enolate.