283584-96-3

Upstream product

• 93-89-0 benzoic acid ethyl ester 
• 1015-28-7 dimethyl (2-oxo-2-phenylethyl)phosphonate 
• 6048-29-9 triphenylphenacylphosphonium bromide 
• 146801-38-9 (E)-4,4,4-trifluoro-1,3-diphenyl-2-buten-1-one 
• 434-45-7 2,2,2-Trifluoroacetophenone 

Downstream Products

• 146801-38-9 (E)-4,4,4-trifluoro-1,3-diphenyl-2-buten-1-one 
• 1020171-83-8 (R)-4,4,4-trifluoro-1,3-diphenylbutan-1-one 
• 1392505-17-7 (E)-4,4,4-trifluoro-1,3-diphenyl(1-D)-2-buten-1-ol 
• 1392505-46-2 4,4,4-(E)-[3-D]-4,4,4-trifluoro-1,3-diphenylbutan-1-one 
• 1020172-05-7 (3R)-4,4,4-trifluoro-1,3-diphenylbutan-1-ol 

Relevant academic research and scientific papers

Base-promoted isomerization of CF3-containing allylic alcohols to the corresponding saturated ketones under metal-free conditions

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.

Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing

A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.

Ruthenium-catalyzed one-pot tandem isomerization-transfer hydrogenation reactions of γ-trifluoromethylated allylic alcohols and β-trifluoromethylated enones

The ruthenium-2-propanol combination was found to transform γ-trifluoromethylated allylic alcohols and β-trifluoromethylated enones into the corresponding saturated alcohols in excellent yields via a one-pot tandem process involving isomerization and transfer hydrogenation(s). High stereospecificity was demonstrated and evidence for two mechanistic pathways is provided. The method was applied to a rapid synthesis of trifluoromethylated citronellol. Copyright

Synthesis of β-CF3 ketones from trifluoromethylated allylic alcohols by ruthenium catalyzed isomerization

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

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

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.