113307-19-0Relevant articles and documents
An Expedient Stereoselective Access to (Z)-2-Fluoroalkenoates
Clemenceau, Denis,Cousseau, Jack
, p. 6903 - 6906 (1993)
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.
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
Z-selective or stereospecific alkenylation reaction: A novel synthetic method for α-fluoro-α,β-unsaturated esters
Yoshimatsu, Mitsuhiro,Murase, Yoshinori,Itoh, Akinori,Tanabe, Genzoh,Muraoka, Osamu
, p. 998 - 999 (2007/10/03)
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