76886-34-5Relevant academic research and scientific papers
Rhodium-catalyzed addition of alcohols to terminal enones
Farnworth, Marc V.,Cross, Michael J.,Louie, Janis
, p. 7441 - 7443 (2004)
[Rh(COD)(OMe)]2 was found to catalyze the addition of aliphatic and aromatic alcohols with terminal enones to afford β-alkoxyketones in high yields.
Mild Cu-Catalyzed Oxidation of Benzylic Boronic Esters to Ketones
Grayson, James D.,Partridge, Benjamin M.
, p. 4296 - 4301 (2019/05/14)
The oxidation of benzylic boronic esters directly to the ketone is reported. This mild Cu-catalyzed method uses an ambient atmosphere of air as the terminal oxidant and is notably chemoselective. Oxidation of the C-B bond occurs selectively, even in the presence of unprotected alcohols. Initial investigation suggests the reaction proceeds through an alkylboron to Cu transmetalation, peroxide formation, and rearrangement to give the carbonyl.
Acid catalyzed rearrangement of vinyl and ketene acetals
Maziarz, Elzbieta,Furman, Bart?omiej
, p. 1651 - 1658 (2014/02/14)
Substituted vinyl and ketene acetals undergo smooth oxygen-to-carbon rearrangement with a catalytic amount of TMSOTf to afford chain-extended ketones or esters, respectively. The developed procedure has been applied to the stereoselective synthesis of C-glycosides from the corresponding anomeric vinyl ethers.
Oxa-Michael addition promoted by the aqueous sodium carbonate
Guo, Shi-Huan,Xing, Sheng-Zhu,Mao, Shuai,Gao, Ya-Ru,Chen, Wen-Liang,Wang, Yong-Qiang
supporting information, p. 6718 - 6720 (2014/12/11)
An efficient Michael addition of alcohols to activated alkenes promoted by sodium carbonate with water as reaction medium has been developed. The reaction provides a general, economical and environmentally friendly approach for the synthesis of β-alkoxycarbonyl compounds.
Evidence That Protons Can Be the Active Catalysts in Lewis Acid Mediated Hetero-Michael Addition Reactions
Wabnitz, Tobias C.,Yu, Jin-Quan,Spencer, Jonathan B.
, p. 484 - 493 (2007/10/03)
The mechanism of Lewis acid catalysed hetero-Michael addition reactions of weakly basic nucleophiles to α,β-unsaturated ketones was investigated. Protons, rather than metal ions, were identified as the active catalysts. Other mechanisms have been ruled out by analyses of side products and of stoichiometric enone-catalyst mixtures and by the use of radical inhibitors. No evidence for the involvement of π-olefin-metal complexes or for carbonyl-metal-ion interactions was obtained. The reactions did not proceed in the presence of the non-coordinating base 2,6-di-tert-butylpyridine. An excellent correlation of catalytic activities with cation hydrolysis constants was obtained. Different reactivities of mono- and dicarbonyl substrates have been rationalised. A 1H NMR probe for the assessment of proton generation was established and Lewis acids have been classified according to their propensity to hydrolyse in organic solvents. Bronsted acid-catalysed conjugate addition reactions of nitrogen, oxygen, sulfur and carbon nucleophiles are developed and implications for asymmetric Lewis acid catalysis are discussed.
TRIMETHYLSILYL TRIFLATE CATALYZED ALDOL-TYPE REACTION OF ENOL SILYL ETHERS AND ACETALS OR RELATED COMPOUNDS
Murata, Shizuaki,Suzuki, Chikusa,Noyori, Ryoji
, p. 4259 - 4276 (2007/10/02)
Trimethylsilyl triflate with or without added hindered tertiary amines catalyzes directed condensation of enol trimethylsilyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds.R
TRIMETHYLSILYL TRIFLATE IN ORGANIC SYNTHESIS
Noyori, R.,Murata, S.,Suzuki, M.
, p. 3899 - 3910 (2007/10/02)
Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media.The reactions proceed via one-center, electrophilic coordination of the silyl group to hetero functional groups and exhibit unique selectivities.
CONDENSATION OF ENOL SILYL ETHERS AND DIALKOXYMETHANES CATALYZED BY TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE. REGIOSPECIFIC SYNTHESIS OF α-ALKOXYMETHYL KETONES
Murata, S.,Suzuki, M.,Noyori, R.
, p. 2527 - 2528 (2007/10/02)
A facile, regiospecific entry to α-alkoxymethyl ketones is described.
