2245-25-2Relevant articles and documents
Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines
Cabré, Albert,Cabezas-Giménez, Juanjo,Sciortino, Giuseppe,Ujaque, Gregori,Verdaguer, Xavier,Lledós, Agustí,Riera, Antoni
supporting information, p. 3624 - 3631 (2019/07/10)
The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).
Selective Aerobic Oxygenation of Tertiary Allylic Alcohols with Molecular Oxygen
Zhu, Bencong,Shen, Tao,Huang, Xiaoqiang,Zhu, Yuchao,Song, Song,Jiao, Ning
supporting information, p. 11028 - 11032 (2019/07/08)
Aerobic epoxidation of tertiary allylic alcohols remains a significant challenge. Reported here is an efficient and highly chemoselective copper-catalyzed epoxidation and semipinacol rearrangement reaction of tertiary allylic alcohols with molecular oxygen. The solvent 1,4-dioxane activates dioxygen, thereby precluding the addition of a sacrificial reductant.
Isomerization of terminal epoxides by a [Pd-H] catalyst: A combined experimental and theoretical mechanistic study
Vyas, Devendra J.,Larionov, Evgeny,Besnard, Celine,Guenee, Laure,Mazet, Clement
supporting information, p. 6177 - 6183 (2013/06/04)
An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.
Practical corey-chaykovsky epoxidation: Scope and limitation
Yu, Hao,Deng, Xiaobing,Cao, Shengli,Xu, Jiaxi
experimental part, p. 509 - 514 (2012/04/11)
Corey-Chaykovsky epoxidation is one of the versatile methods for synthesis of structurally diverse oxiranes. The extension of simplified Corey-Chaykovsky epoxidation has been investigated. Ketones and aromatic aldehydes were epoxidized in satisfactory to excellent yields with trimethylsulfonium iodide as an ylide precursor and crushed potassium hydroxide as a base in tertiary butanol.The scope and limitation of the simplified procedure were examined. The results revealed that the procedure is applicable to the epoxidation of ketones and aromatic aldehydes.
An improved preparation of epoxides from carbonyl compounds by using diiodomethane/methyllithium: Synthetic applications
Concellón, José M,Cuervo, Humildad,Fernández-Fano, Ramón
, p. 8983 - 8987 (2007/10/03)
Synthesis of epoxides starting from different carbonyl compounds is easily carried out by using a diiodomethane and methyllithium at 0°C and a short reaction time. Starting from α-aminoaldehydes the reaction affords amino epoxides, with high diastereoselectivity. The products were transformed into 1,3-diaminoalkan-2-ols by treatment with different amines.
Solvent free synthetic procedure throughout reaction and separation: ylide reaction with alkyl aryl ketones in the absence of solvent followed by distillation to give 1-alkyl-1-aryloxiranes
Toda, Fumio,Kanemoto, Kazuyuki
, p. 185 - 188 (2007/10/03)
After heating a mixture of trimethylsulphonium iodide, tBuOK and an alkyl aryl ketone at 60-70 °C for 1-5 h, vacuum distillation gave the corresponding 1-alkyl-1-aryloxirane. The procedure was accomplished without using any solvent throughout the reaction and the separation.
New synthetic routes to 2-fluoro-2-phenylalkanoic acids
Goj, Olav,Haufe, Guenter
, p. 1289 - 1294 (2007/10/03)
2-Fluoro-2-phenylalkanoic acids 2 are obtained by oxidation of the corresponding β-fluoro-β-phenyl alcohols 6. These compounds are shown to be accessible by two alternative pathways, either by bromo fluorination of α-alkyl styrenes 3, subsequent bromine-b
