Formaldehyde SAMP-hydrazone as a neutral chiral formyl anion and cyanide equivalent: Asymmetric Michael additions to nitroalkenes

Article abstract of DOI:10.1055/s-1996-4174

The enantioselective synthesis of α-substituted β-nitro nitriles 4 and β-nitroaldehydes 5 by Michael addition of formaldehyde SAMP-hydrazone 1 to nitroalkenes 2 in excellent overall yields and high enantiomeric excesses(ee = 90- > 99%) is described. Compound 1 constitutes a neutral chiral formyl anion and cyanide equivalent. The absolute configuration was determined by X-ray structure analysis of the crystalline SAMP-hydrazone 1,4-adduct 3e.