101128-06-7Relevant articles and documents
Synthese stereoselective d'esters α,β-ethyleniques α-fluores E par reaction de Wittig-Horner a partir du diethyl phosphono α-fluoroacetate de methyle. Etude comparative avec le diphenyl phosphonoxy α-fluoroacetate de methyle
Etemad-Moghadam, Guita,Seyden-Penne, Jacqueline
, p. 448 - 454 (2007/10/02)
The reaction of methyl diethylphosphono α-fluoroacetate with aliphatic,α,β-ethylenic or aromatic aldehydes in the presence of nBuLi in THF at -78 deg C gives E α-fluoro esters with a very high stereoselectivity and a good yield.At 20 deg C, the stereoselectivity is not so high.From the corresponding phosphine oxide, the reaction is less stereoselective favoring the E ester from aliphatic aldehydes and the Z one from α,β- unsaturated aldehydes or PhCHO. These results are in line with the previous interpretations taking into account the electron density and steric hindrance around the phosphorus atom.