79909-17-4Relevant academic research and scientific papers
General and efficient α-oxygenation of carbonyl compounds by TEMPO induced by single-electron-transfer oxidation of their enolates
Dinca, Emanuela,Hartmann, Philip,Smrcek, Jakub,Dix, Ina,Jones, Peter G.,Jahn, Ullrich
supporting information, p. 4461 - 4482 (2012/10/30)
A generally applicable method for the synthesis of protected α-oxygenated carbonyl compounds is reported. It is based on the single-electron-transfer oxidation of easily generated enolates to the corresponding α-carbonyl radicals. Coupling with the stable free radical TEMPO provides α-(piperidinyloxy) ketones, esters, amides, acids or nitriles in moderate-to-excellent yields. Enolate aggregates influence the outcome of the oxygenation reactions significantly. Competitive reactions have been analyzed and conditions for their minimization are presented. Chemoselective reduction of the products led to either N-O bond cleavage to α-hydroxy carbonyl compounds or reduction of the carbonyl functionality tomonoprotected 1,2-diols or O-protected amino alcohols. The oxygenation of enolates proves to be the most general and effective methodology for the synthesis of O-protected α-oxy carbonyl compounds and nitriles A. The scope and limitations of the electron-transfer-induced radical coupling reaction with TEMPO are presented. The reaction pathways are outlined. Methods for the deprotection to α-hydroxy carbonyl compounds B are provided and discussed. Copyright
Medicinal Plants of Southern Africa. Part 4. Synthesis of Brackenin-like Molecules from 1,4-Dicarbonyl Precursors and by Oxydative Coupling. X-Ray Molecular Structure of Racemic-2,3-Dibenzyl-1,4-diphenylbutane-1,4-dione
Drewes, Siegfried E.,Hogan, Craig J.,Kaye, Perry T.,Roos, Gregory H. P.
, p. 1585 - 1591 (2007/10/02)
Oxidative coupling of appropriate trimethylsilyl enol ethers is shown to give 1,4-diaryl-1,4-diketones in acceptable yields.Subsequent dibenzylation of these intermediates affords compounds related to the naturally occuring brackenin (1).Examination of these products by 1H n.m.r. and 13C n.m.r. demonstrates that these techniques can be used for the determination of relative configurations without resorting to X-ray crystallography.
DIANION OF DIETHYL SUCCINATE: REACTIONS WITH ALKYLATING AGENTS AND CARBONYL COMPOUNDS
Pohmakotr, Manat,Reutrakul, Vichai,Phongpradit, Tipparat,Chansri, Arayan
, p. 687 - 690 (2007/10/02)
Dianion of diethyl succinate reacted readily with alkylating agents and carbonyl compounds to give α,β-dialkylsubstituted diethyl succinate and paraconic esters respectively.The conversion of some paraconic esters into 4-carboethoxycyclopentenones was als
