32541-57-4Relevant academic research and scientific papers
Simple access to β-trifluoromethyl-substituted ketones via copper-catalyzed ring-opening trifluoromethylation of substituted cyclopropanols
Kananovich, Dzmitry G.,Konik, Yulia A.,Zubrytski, Dzmitry M.,J?rving, Ivar,Lopp, Margus
supporting information, p. 8349 - 8352 (2015/05/13)
Tertiary cyclopropanols react rapidly with Togni reagent in methanol at room temperature in the presence of catalytic amounts (3 mol%) of CuCl affording β-trifluoromethyl ketones in 65-73% isolated yields. Ring opening in 1,2-dialkylsubstituted cyclopropanols gives a mixture of isomeric β-trifluoromethyl ketones in about 50% combined yield.
Gold- and silver-catalyzed reactions of propargylic alcohols in the presence of protic additives
Pennell, Matthew N.,Turner, Peter G.,Sheppard, Tom D.
experimental part, p. 4748 - 4758 (2012/05/04)
A wide range of primary, secondary and tertiary propargylic alcohols undergo a Meyer-Schuster rearrangement to give enones at room temperature in the presence of a gold(I) catalyst and small quantities of MeOH or 4-methoxyphenylboronic acid. The syntheses of the enone natural products isoegomaketone and daphenone were achieved using this reaction as the key step. The rearrangement of primary propargylic alcohols can readily be combined in a one-pot procedure with the addition of a nucleophile to the resulting terminal enone, to give β-aryl, β-alkoxy, β-amino or β-sulfido ketones. Propargylic alcohols bearing an adjacent electron-rich aryl group can also undergo silver-catalyzed substitution of the alcohol with oxygen, nitrogen and carbon nucleophiles. This latter reaction was initially observed with a batch of gold catalyst that was probably contaminated with small quantities of silver salt.
REACTION DES VINYLOGUES D'HEMIACETALS ET DE LEURS EQUIVALENTS SYNTHETIQUES SUR LES ETHERS D'ENOLS HETEROCYCLIQUES
Poirier, Jean-Marie,Dujardin, Gilles
, p. 3337 - 3340 (2007/10/02)
We describe the reaction of hemiacetal vinylogs 2 or their synthetic equivalent with cyclic enol ethers 1 yielding ketoacetals 3.Acidic treatment of these compounds leads to bicyclic heterocycles 8 or enone aldehyde 12 depending on the nature of substituents R1.
