Diastereo- and enantioselective synthesis of vicinal diamines via aza-Michael addition to nitroalkenes

Article abstract of DOI:10.1055/s-1996-4411

The asymmetric synthesis of protected 1,2-diamines 4 by aza-analogous Michael addition of (-)-(2S,3R,4R,5S)-1-amino-3,4-dimethoxy-2,5-bis(methoxymethyl)pyrrolid ine (ADMP) to nitroalkenes 1 in good overall yields and high enantiomeric excesses (ee = 93-96%) is described. The auxiliary constitutes a novel chiral equivalent of ammonia and is removed under reductive N-N bond cleavage with Raney nickel, which also reduces the nitro group. The absolute configuration was determined by NMR-spectroscopic methods and polarimetry.