Chemoselective conversion of conjugated nitroalkenes into ketones by sodium borohydride-hydrogen peroxide: A new synthesis of 4-oxoalkanoic acids, dihydrojasmone and (±)exo-brevicomin

Article abstract of DOI:10.1055/s-1994-25557

A new, simple, cheap, and practical procedure for the direct transformation of α,β-unsaturated nitroalkenes into ketones has been realized by the NaBH₄/H₂O₂ system. By this method, other functional groups such as C-C double bonds, ketals or aromatic nitro groups were preserved. Application of this methodology to the preparation of 4-oxoalkanoic acids, dihydrojasmone, and (±)-exobrevicomin is also reported.