Nitroalkanes as a new source of 2-alkylidene-1,4-diols, in two steps

Article abstract of DOI:10.1016/S0040-4020(99)00829-7

A variety of 2-alkylidene-1,4-diols have been conveniently prepared, in two steps, by conjugate addition of a nitroalkane to the appropriate enedione derivatives under basic conditions (DBU), followed by chemoselective reduction (LiAlH₄/Et₂O) of the carbonyl functionalities of the Michael adduct, obtained after elimination of nitrous acid.