26927-86-6Relevant articles and documents
A facile and mild approach for stereoselective synthesis of α-fluoro-α,β-unsaturated esters from α-fluoro-β-keto esters via deacylation
Qian, Jinlong,Yi, Wenbin,Lv, Meifang,Cai, Chun
, p. 127 - 132 (2015/02/02)
The highly stereoselective olefination reaction of α-fluoro-β-keto esters for the synthesis of α-fluoro-α,β-unsaturated esters has been developed. The olefination combines nucleophilic addition, intramolecular nucleophilic addition, and elimination in one step, as well as provides a facile synthetic approach to α-fluoro-α,β-unsaturated esters which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.
A convenient method for the synthesis of (Z)-α-fluoroacrylates: Lewis base-catalyzed carbonyl fluoroolefination using fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal
Michida, Makoto,Mukaiyama, Teruaki
, p. 890 - 891 (2008/12/22)
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
Microwave-assisted one-pot synthesis of α-fluoro-α,β- unsaturated esters under solvent-free conditions
Ren, Aishan,Yang, Xiongjun,Hong, Jing,Yu, Xiaochun
experimental part, p. 2376 - 2378 (2009/05/27)
A microwave-assisted approach for the synthesis of α-fluoro-α, β-unsaturated esters from ethyl bromofluoroacetate, aldehydes, and triphenylphosphine in the presence of Zn-Cu under solvent-free conditions was achieved. The reaction was accomplished within
CFC- or HFC-free approach to α-substituted β,γ,γ-trifluoroallyl alcohols by the reaction of β-fluoro-β-trifluoromethylated enol tosylate with Grignard reagents
Funabiki, Kazumasa,Sawa, Ken-Ichi,Shibata, Katsuyoshi,Matsui, Masaki
, p. 1134 - 1136 (2007/10/03)
The reaction of β-fluoro-β-trifluoromethylated enol tosylate with Grignard reagents giving the corresponding β,γ,γ-trifluoroallyl alcohols as well as heteropoly acid-mediated ethanolysis of the allyl alcohols affording (Z)-β-substituted α-fluoro-α,β-unsaturated esters is described.
A novel reaction of β,β'-dihydroxy acids or esters with vanadium(V) trichloride oxide. New entry to the stereoselective synthesis of α-fluoro- α,β-unsaturated acids and esters
Ishihara, Takashi,Shintani, Atsuhiro,Yamanaka, Hiroki
, p. 4865 - 4868 (2007/10/03)
β,β'-Dihydroxy carboxylic acids and esters, readily prepared from dibromofluoroacetate and aldehydes, underwent deoxygenation, followed by elimination of aldehyde by the action of vanadium(V) trichloride oxide at the reflux temperature of chlorobenzene fo
Zinc-Diethylaluminium Chloride Induced Coupling Reaction of Dibromofluoroacetate with Carbonyl Compounds. New Efficient and Selective Synthesis of α-Bromo-α-fluoro-β-hydroxy and α-Fluoro-β,β'-dihydroxy Esters
Ishihara, Takashi,Matsuda, Takayuki,Imura, Katsunori,Matsui, Hirofumi,Yamanaka, Hiroki
, p. 2167 - 2170 (2007/10/02)
Treatment of ethyl dibromofluoroacetate with aldehydes or ketone in the presence of zinc and diethylaluminium chloride at -20 deg C gave rise to the corresponding α-bromo-α-fluoro-β-hydroxy alkanoic acid ethyl esters in good yields, while the use of two equivalents each of aldehyde, zinc, and diethylaluminium chloride in the reaction resulted in a double coupling reaction affording the 1:2 adducts, α-fluoro-β,β'-dihydroxy esters in high yields.
A convenient palladium-catalyzed synthesis of α-fluoro-α,β-unsaturated esters
Shen, Yanchang,Zhou, Yuefen
, p. 247 - 251 (2007/10/02)
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.
