146801-46-9Relevant academic research and scientific papers
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
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
Palladium-catalyzed regio- and stereoselective formate reduction of fluorine-containing allylic mesylates. A new entry for the construction of a tertiary carbon attached with a fluoroalkyl group
Konno, Tsutomu,Takehana, Tsuyoshi,Mishima, Makoto,Ishihara, Takashi
, p. 3545 - 3550 (2007/10/03)
The regioselective palladium-catalyzed formate reduction of γ-fluoroalkylated allylic esters is described. Reduction of the allylic esters under the influence of palladium with a monodentate phosphine ligand proceeded preferentially at the γ position, the corresponding reduction products with a fluoroalkyl group at the tertiary carbon being afforded in high yields. When the chiral allylic ester was employed, complete chirality transfer was observed, leading to the optically active materials in high yields.
Aldol condensation of trifluoroacetophenone and acetone: Testing a prediction
Guthrie, J. Peter,Barker, Jonathan A.
, p. 6698 - 6703 (2007/10/03)
Rate and equilibrium constants have been determined for both stages of the aldol condensation of acetone with trifluoroacetophenone. The extensive hydration of trifluoroacetophenone and the acid dissociation of the hydrate complicated the kinetic analysis. Dehydration of the intermediate ketol leads to two enones which equilibrate in base more rapidly than they undergo hydration to the ketol. This is consistent with interconversion via the enolate of the ketol, which loses OH- faster than it undergoes C-protonation. The rate constant determined for the aldol addition step is in satisfactory agreement with the value predicted from a Marcus correlation (J. Am. Chem. Sec. 1991, 113, 7249-7255).
