59161-52-3Relevant academic research and scientific papers
Selective intermolecular oxidative cross-coupling of enolates
Amaya, Toru,Maegawa, Yusuke,Masuda, Takaya,Osafune, Yuma,Hirao, Toshikazu
, p. 10072 - 10075 (2015)
Selective intermolecular oxidative cross-coupling of enolates, which is a bond-forming reaction between carbanion equivalents, remains as an unsolved issue despite its potential utility for the direct synthesis of unsymmetrical 1,4-diones. The main difficulty derives from the unavoidable homo-coupling. Our strategy depends on the selective one-electron oxidation of one enolate to afford an electrophilic carbonyl α-radical species, followed by trapping with another enolate. The present study demonstrates the selective oxovanadium(V)-induced cross-coupling between boron and silyl enolates.
Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
Jagtap, Pratap R.,Císa?ová, Ivana,Jahn, Ullrich
supporting information, p. 750 - 755 (2018/02/09)
A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
Vanadium(V)-Induced Oxidative Cross-Coupling of Various Boron and Silyl Enolates
Amaya, Toru,Osafune, Yuma,Maegawa, Yusuke,Hirao, Toshikazu
, p. 1301 - 1304 (2017/06/23)
Intermolecular oxidative cross-coupling of two different enolates is one of the most useful reactions to synthesize unsymmetrical 1,4-dicarbonyl compounds. In this study, the oxovanadium(V)-induced intermolecular oxidative cross-coupling of enolates afforded unsymmetrical 1,4-dicarbonyl compounds. Various boron and silyl enolates underwent the formation of ketone–ester, ester–ketone, ester–ester, amide–ketone and amide–ester coupling products. These results clearly show the versatility of the present oxidative cross-coupling protocol.
Oxovanadium(v)-induced diastereoselective oxidative homocoupling of boron enolates
Amaya, Toru,Masuda, Takaya,Maegawa, Yusuke,Hirao, Toshikazu
supporting information, p. 2279 - 2281 (2014/03/21)
Oxovanadium(v)-induced dl-selective oxidative coupling of (Z)-boron enolate was demonstrated to give the corresponding 2,3-disubstituted 1,4-diketone in a good yield. High selectivity (up to 94:6) was attained when the reaction was performed with VO(OPr-i)2Cl at -30 °C. The Royal Society of Chemistry 2014.
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.
