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Synthesis 1996; 1996(12): 1443-1450
DOI: 10.1055/s-1996-4411
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Diastereo- and Enantioselective Synthesis of Vicinal Diamines via Aza-Michael Addition to Nitroalkenes

Dieter Enders* , Jürgen Wiedemann
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax +49(241)8888127; E-mail: Enders@RWTH-Aachen.de
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Publication Date:
31 December 2000 (online)

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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)pyrrolidine (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.

vicinal diamines - asymmetric synthesis - nitroalkenes - Michael addition - chiral ammonia equivalent

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