851645-63-1Relevant academic research and scientific papers
Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions
Hamada, Yoko,Kawasaki-Takasuka, Tomoko,Yamazaki, Takashi
, p. 1507 - 1512 (2017/08/14)
Following to the computational expectation, our previously reported intriguing 1,3-proton shift of 4,4,4-trifluorobut-2-yn-1-ols was successfully extended to the 4,4,4-trifluorobut-2-en-1-ol system under metal-free conditions to afford the corresponding saturated ketones in high to excellent chemical yields using such a convenient and easy-to-handle base as DBU at the toluene refluxing temperature, and utilization of the corresponding optically active substrates unambiguously demonstrated that this transformation proceeded in a highly stereoselective fashion.
Catalytic Enantioselective Conjugate Alkynylation of β-Aryl-β-trifluoromethyl Enones Constructing Propargylic All-Carbon Quaternary Stereogenic Centers
Sanz-Marco, Amparo,Blay, Gonzalo,Vila, Carlos,Pedro, José R.
supporting information, p. 3538 - 3541 (2016/08/16)
The enantioselective conjugate alkynylation of β-aryl-β-trifluoromethyl enones has been carried out using terminal alkynes and diethylzinc in the presence of 3,3′-bis(perfluorophenyl)BINOL as the chiral ligand to give the corresponding ketones bearing a t
Efficient and highly enantioselective construction of trifluoromethylated quaternary stereogenic centers via high-pressure mediated organocatalytic conjugate addition of nitromethane to β,β-disubstituted enones
Kwiatkowski, Piotr,Cholewiak, Agnieszka,Kasztelan, Adrian
supporting information, p. 5930 - 5933 (2015/01/09)
A very effective high-pressure-induced acceleration of asymmetric organocatalytic conjugate addition of nitromethane to sterically congested β,β-disubstituted β-CF3 enones has been developed. A combination of pressure (8-10 kbar) and noncovalent catalysis with low-loading of chiral tertiary amine-thioureas (0.5-3 mol %) is shown to provide very efficient access to a wide range of γ-nitroketones containing trifluoromethylated all-carbon quaternary stereogenic centers in the β-position (80-97%, 92-98% ee).
Synthesis of β-CF3 ketones from trifluoromethylated allylic alcohols by ruthenium catalyzed isomerization
Bizet, Vincent,Pannecoucke, Xavier,Renaud, Jean-Luc,Cahard, Dominique
supporting information, p. 56 - 61 (2013/11/06)
This work describes the optimization process for the synthesis of β-trifluoromethylated ketones from trifluoromethylated allylic alcohols. This transformation proceeds through a ruthenium catalyzed isomerization under mild conditions with high atom econom
Ruthenium-catalyzed redox isomerization of trifluoromethylated allylic alcohols: Mechanistic evidence for an enantiospecific pathway
Bizet, Vincent,Pannecoucke, Xavier,Renaud, Jean-Luc,Cahard, Dominique
supporting information; experimental part, p. 6467 - 6470 (2012/07/27)
Transfer news: A synthetic approach to chiral β-CF3- substituted saturated carbonyl compounds has been developed in which ruthenium complexes efficiently catalyze the redox isomerization of CF3-bearing allylic alcohols by an intramol
Enantioselective synthesis of trifluoromethyl-substituted 2-isoxazolines: Asymmetric hydroxylamine/enone cascade reaction
Matoba, Kazutaka,Kawai, Hiroyuki,Furukawa, Tatsuya,Kusuda, Akihiro,Tokunaga, Etsuko,Nakamura, Shuichi,Shiro, Motoo,Shibata, Norio
supporting information; experimental part, p. 5762 - 5766 (2010/11/03)
(Figure Presented) Cuts both ways: The title reaction consists of an addition/cyclization/dehydration sequence and affords the biologically important chiral 3,5-diaryl-5-(trifluoromethyl)-2-isoxazolines 1 in excellent yields with high ee values. The flexi
New approaches to β-trifluoromethylated enone derivatives
Jeong, In Howa,Jeon, Sung Lan,Kim, Myong Sang,Kim, Bum Tae
, p. 1629 - 1638 (2007/10/03)
β-Trifluoromethylated enaminones 1 were prepared stereospecifically or high stercoselectively in 31-92% yields from the reaction of Weinreb amides with trifluoropropynyl lithium, followed by quenching with H2O in the presence of amine derivativ
