113307-19-0

Upstream product

• 864363-35-9 (E)-2-Fluoro-3-hydroxy-5-phenyl-2-phenylselanyl-pent-4-enoic acid ethyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 459-72-3 ethyl 2-fluoroacetate 
• 401-55-8 ethyl bromofluoroacetate 
• 28620-50-0 α-(trans-2-phenyl-ethenyl)-N-phenylnitrone 
• 4392-24-9 Cinnamyl bromide 
• 910803-66-6 ethyl α-(1,3-benzothiazol-2-ylsulfonyl)-α-fluoroacetate 
• 7582-61-8 diethyl 2-oxo-3-fluorobutan-1,4-dioate sodium salt 
• 401-58-1 ethyl 2-fluoro-2-iodoacetate 

Relevant academic research and scientific papers

An Expedient Stereoselective Access to (Z)-2-Fluoroalkenoates

The reaction between an aldehyde R-CHO and diethyl 2-oxo-3-fluorobutan-1,4-dioate as its sodium salt EtO2C-CO-CF-CO2Et-,Na+ mainly leads in THF to (Z)-2-fluoroalkenoates R-CH=CF-CO2Et (Z/E>/=80/20), the Z-stereoselectivity depending on the bulk of the R group.Key words: 2-Fluoroalkenoates; (Z)-stereoselective synthesis.

Stereoselective synthesis of fluoroalkenoates and fluorinated isoxazolidinones: N-substituents governing the dual reactivity of nitrones

α-Fluoroalkenoates and 4-fluoro-5-isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones by the reactions between nitrones and α-fluoro-α-bromoacetate. By altering N-substituents in nitrones, (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones can be achieved, respectively, with high chemo- and stereoselectivities. Experimental and computational studies have been conducted to elucidate the reaction mechanisms. Linear free energy relationship studies further revealed that the N-substituent effects are primarily of electronic origin. Copyright

A convenient method for the synthesis of (Z)-α-fluoroacrylates: Lewis base-catalyzed carbonyl fluoroolefination using fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal

A highly useful method is established for the stereoselective synthesis of (Z)-α-fluoroacrylates from various aldehydes and fluoro(trimethylsilyl) ketene ethyl trimethylsilyl acetal in the presence of a Lewis base catalyst. The ketene acetal, easily prepared from ethyl fluoroacetate, affords α-fluoroacrylates in high yields with excellent Z stereoselectivities under mild conditions. Copyright

Exceptionally mild, high-yield synthesis of α-fluoro acrylates

Novel achiral and chiral alkyl α-(1,3-benzothiazol-2-ylsulfonyl)- α-fluoroacetates can be readily synthesized by metalation-fluorination of (1,3-benzothiazol-2-ylsulfonyl)acetates. DBU-mediated condensations of these fluorinated synthons with aldehydes proceed in a facile manner at 0 °C or at room temperature giving high yields of α-fluoro acrylates. Ketones are unreactive under these conditions. The presence of fluorine renders the synthon substantially more reactive compared to the unfluorinated analogue. Reactivity of α-(1,3-benzothiazol-2-ylsulfonyl)-α-fluoroacetate and the Horner-Wadsworth-Emmons reagent (EtO)2P(O)CHFCOOEt has also been compared.

Z-selective or stereospecific alkenylation reaction: A novel synthetic method for α-fluoro-α,β-unsaturated esters

The Z-selective formation of α-fluoro-α,β-unsaturated esters was achieved using the deselenenic acid of the syn-and/or anti-3-aryl-2-fluoro-3-hydroxy-2-organoselanylacetates 3 and 4 with trifluoromethanesulfonic acid. In contrast, the 3-alkyl-substituted propanoates 3f and 4b stereospecifically underwent alkenylation to give the (E)- or (Z)-α-fluoro-α,β-unstaurated esters 5f. We were also successful in the one-pot alkenylation reactions. Copyright

A convenient palladium-catalyzed synthesis of α-fluoro-α,β-unsaturated esters

During the treatment of ethyl α-fluoro-α-iodoacetate with aldehydes in the presence of tri-n-butylarsine and a catalytic amount (10 molpercent) of Pd(PPh3)4, the aldehydes were eventually completely consumed and α-fluoro-α,β-unsaturated esters were obtained in 52-90percent yield.

ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC COMPOUNDS. 3. REGIOSELECTIVE ANODIC MONOFLUORINATION OF ORGANOSELENIUM COMPOUNDS AND THEIR SYNTHETIC APPLICATION

Regioselective anodic α-monofluorination of selenides bearing electron-withdrawing groups such as cyano, ester, and amide groups was successfully performed.Highly stereoselective synthesis of α-fluoro α,β-unsaturated esters was achieved by using an α-fluo