Henry reaction of fluorinated nitro compounds

The Henry (nitroaldol) reaction of fluorinated nitro compounds with various aromatic aldehydes and a fluorinated aliphatic aldehyde to give β-fluoro-β-nitroalcohols which bearing a fluorinated quaternary carbon center was reported. The relative configuration of the major diastereoisomer of 2-fluoro-2-nitro-1-(4-nitrophenyl)-3-phenylpropanol (5bf) was determined by X-ray single crystal analysis.

Henry reaction of α-fluoro nitro compounds with various aldehydes gave fluorinated nitroalcohols in moderate to good yields.Figure optionsDownload as PowerPoint slideHighlights
► An organocatalytic Henry reaction of fluoro nitro compounds was described.
► β-Fluoro-β-nitroalcohols bearing a fluorinated quaternary carbon center were obtained.
► The relative configurations of products were determined using X-ray and NMR analysis.