147410-72-8Relevant academic research and scientific papers
New reaction mode of the Horner-Wadsworth-Emmons reaction for the preparation of α-fluoro-α,β-unsaturated esters
Sano, Shigeki,Ando, Tsuyoshi,Yokoyama, Kenji,Nagao, Yoshimitsu
, p. 777 - 779 (1998)
Excellent E-selectivity was observed in the Horner-Wadsworth-Emmons (HWE) reactions of ethyl 2-fluoro-2-diethylphosphonoacetate 1 with alkyl aryl ketones 2a-f using Sn(OSO2CF3)2 and N-ethylpiperidine. Mg(II)-promoted HWE r
Stereoselective formation of (Z)-2-fluoroalkenoates via Julia-Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones
Larnaud, Florent,Pfund, Emmanuel,Linclau, Bruno,Lequeux, Thierry
, p. 5632 - 5639 (2015/03/30)
The selective synthesis of fluoroalkenoates is reported from a pyrimidinyl fluorosulfone. This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle
Tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates and a synthetic approach to Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly dipeptide isostere
Sano, Shigeki,Kuroda, Yoko,Saito, Katsuyuki,Ose, Yukiko,Nagao, Yoshimitsu
, p. 11881 - 11890 (2007/10/03)
(Z)-α-Fluoro-α,β-unsaturated esters (Z)-7a-f were stereoselectively prepared by a tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2-phosphonoacetates 6a-f with NaBH4 in EtOH. A concise synthesis of Cbz-Gly-Ψ[(Z)-CF{double bond, long}C]-Gly (26) as a dipeptide isostere was achieved via the tandem reduction-olefination of the corresponding 2-acyl-2-fluoro-2-phosphonoacetate 20.
Efficient synthesis of fluoroalkenes via diethylzinc-promoted wittig reaction
Zoute, Ludivine,Dutheuil, Guillaume,Quirion, Jean-Charles,Jubault, Philippe,Pannecoucke, Xavier
, p. 3409 - 3418 (2008/02/11)
The synthesis of α-fluoroacrylates and α-bromo-α- fluoroalkenes was achieved in very good yields using aldehydes and ketones, triphenylphosphine, diethylzinc as promoter, and ethyl dibromofluoroacetate or dibromofluoromethane, respectively. A change in th
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
Simmons-Smith reactions of fluoroallyl alcohol derivatives
Morikawa,Sasaki,Mori,Shiro,Taguchi
, p. 3189 - 3193 (2007/10/02)
Simmons-Smith reactions of fluoroallyl alcohols and their derivatives with excess Zn-Cu and CH2I2 or Et2Zn and CH2I2 provided fluorocyclopropane derivatives. Diastereoselective cyclopropanation of the
