1020171-85-0

Upstream product

• 851645-63-1 (E)-4,4,4-trifluoro-3-(4-methoxyphenyl)-1-phenyl-2-buten-1-one 
• 1015-28-7 dimethyl (2-oxo-2-phenylethyl)phosphonate 
• 93-89-0 benzoic acid ethyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 3108-34-7 (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one 

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.

One-pot relay reduction-isomerization of β-trifluoromethylated-α,β-unsaturated ketones to chiral β-trifluoromethylated saturated ketones over combined catalysts in aqueous medium

Despite great achievements obtained in tandem reactions, a solution for the incompatible nature of bimetal complexes participating in a multi-step catalytic process is still an unmet challenge. Herein, we utilize a functionalized periodic mesoporous organ

Rhodium(i)-catalyzed 1,4-conjugate arylation toward β-fluoroalkylated electron-deficient alkenes: A new entry to a construction of a tertiary carbon center possessing a fluoroalkyl group

Treatment of β-fluoroalkylated-α,β-unsaturated ketones with 1.2 equiv. of various arylboronic acids in the presence of 5 mol% of [Rh(COD)2]BF4 and 6 mol% of (S)-BINAP in toluene/H 2O (v/v = 4/1) at the reflux temperature for 3 h gave the corresponding Michael adducts in high yields with over 90% enantioselectivity. Though other electron-deficient alkenes, such as vinylsulfone and vinylphosphonate, were found to be much less reactive in the rhodium-catalyzed conjugate addition with arylboronic acids, the reaction of various arylstannanes toward such electron-deficient alkenes took place very smoothly to afford the corresponding adducts in high yields.

A first high enantiocontrol of an asymmetric tertiary carbon center attached with a fluoroalkyl group via Rh(I)-catalyzed conjugate addition reaction

Treatment of fluoroalkylated electron-deficient olefins with various boronic acids in the presence of a catalytic amount of Rh(I) coordinated with (S)-BINAP in toluene/H2O at the reflux temperature for 3 h gave the corresponding conjugate addit