The first general methodology for the gram-scale preparation of previously overlooked β- (hetero) aryl-α-nitro-α, β-enals (3) is reported. Condensation of (hetero) aromatic aldehydes with 2-nitroethanol gave the E-isomers of uncommon β-(hetero) aryl-α-hydroxymethyl-α, β- unsatured-nitroalkenes (2), as determined by NOE and X-ray studies. α-Nitro-α, β-enals 3 were subsequently obtained by hypervalent iodine oxidation of 2 as E− Z-mixtures in solid ...
