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

Abstract

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 (±)-exo-brevicomin is also reported.