Optically active nitroalkenes—synthesis, addition reactions and transformation into amino acids

Optically active nitroalkenes were synthesized via Henry reaction. Conjugate addition of vinylmagnesium bromide to gave nitroalkane while cyclopropanation with sulfur ylides or dibromocarbene afforded nitrocyclopropanes , and in a diastereoselective manner. These products were used to synthesize optically active β-amino acids and as well as cyclopropane γ-amino acids and by reduction of the nitro group and oxidative cleavage of the dioxolane substituent.