6704-35-4Relevant academic research and scientific papers
Electrochemical, Iodine-Mediated α-CH Amination of Ketones by Umpolung of Silyl Enol Ethers
Strehl, Julia,Hilt, Gerhard
supporting information, p. 5968 - 5972 (2020/08/12)
The electrochemical, oxidative Umpolung reaction of silyl enol ethers utilizing simple iodide salts for the synthesis of α-amino ketones is described. The products were isolated in excellent yields of up to 100percent, and various functionalized starting materials were accepted in an undivided electrochemical cell design. Moreover, a sensitivity assessment to ensure an improved reproducibility of the reaction and cyclic voltammetry experiments were performed to postulate a plausible reaction mechanism on their basis.
Glycerol as a Building Block for Prochiral Aminoketone, N-Formamide, and N-Methyl Amine Synthesis
Dai, Xingchao,Rabeah, Jabor,Yuan, Hangkong,Brückner, Angelika,Cui, Xinjiang,Shi, Feng
, p. 3133 - 3138 (2016/11/29)
Prochiral aminoketones are key intermediates for the synthesis of optically active amino alcohols, and glycerol is one of the main biomass-based alcohols available in industry. In this work, glycerol was catalytically activated and purposefully converted with amines to generate highly valuable prochiral aminoketones, as well as N-formamides and N-methyl amines, over CuNiAlOx catalyst. The catalyst structure can be anticipated as nano-Ni species on or in CuAlOx via the formation of nano- Cu?Ni alloy particles. This concept may present a novel and valuable methodology for glycerol utilization.
Highly chemoselective α-diazo carbonyl insertion reactions into N-H and S-H bonds catalysed by [RuCl(η5-C5H5)(PPh3)2]
Del Zotto, Alessandro,Baratta, Walter,Rigo, Pierluigi
, p. 3079 - 3082 (2007/10/03)
Complex [RuCl(η5-C5H5)(PPh3)2], in chloroform at 60 deg C, catalyses the chemoselective insertion of α-diazo carbonyl compounds into N-H and S-H bonds to afford α-keto-amines and α-keto-thioethers.
Retro-aldol and redox reactions of Amadori compounds: Mechanistic studies with variously labeled D-[13C]glucose
Huyghues-Despointes, Alexis,Yaylayan, Varoujan A.
, p. 672 - 681 (2007/10/03)
Oxidation-reduction reactions necessary to justify many of the products observed in Maillard model systems are usually attributed to molecular oxygen and the so-called reductons. The proline specific 1-(1′-pyrrolidinyl)-2-propanone and 1-(1′-pyrrolidinyl)-2-butanone are such compounds that require reduction steps to justify their formation. Experimental evidence using glucose separately labeled at 13C1, 13C2, 13C3, 13C4, 13C5, and 13C6 indicates that 1-(1′-pyrrolidinyl)-2-propanone is formed by two related pathways, initiated by a retro-aldol cleavage of proline Amadori compound at C3-C4, and 1-(1′-pyrrolidinyl)-2-butanone is formed by three pathways, one initiated by a retro-aldol reaction at C2-C3 of the 1-(prolino)-1-deoxy-4-hexosulose (an isomer of Amadori product formed by carbonyl migration) and two others by similar retro-aldol reactions at C4-C5 from both 3-deoxyglucosone and 1-(prolino)-1,4-dideoxy-2,3-hexodiulose. All of the proposed mechanisms require reduction steps for the formation of the target compounds. Model studies have indicated that reductions in Maillard systems can be effected by three pathways: through hydride transfer from formic acid; through cyclic dimerization of α-hydroxy carbonyl compounds followed by electrocyclic ring opening to produce oxidation/reduction products; and by disproportionation of enediols with α-dicarbonyl compounds through double proton transfer.
