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Synthesis 1996; 1996(1): 48-52
DOI: 10.1055/s-1996-4174
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Formaldehyde SAMP-Hydrazone as a Neutral Chiral Formyl Anion and Cyanide Equivalent: Asymmetric Michael Additions to Nitroalkenes

Dieter Enders1 , Ralf Syrig, Gerhard Raabe, Rosario Fernández, Consolación Gasch, José-María Lassaletta2 , José-Manuel Llera
  • 1Institut 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
  • 2Departamento de Química Orgánica, Universidad de Sevilla, Apartado de Correos 553, E-41071 Sevilla, Spain, Fax +34(5)4624960
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Publication Date:
31 December 2000 (online)

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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.

asymmetric synthesis - formyl anion equivalent - Michael addition - Umpolung - SAMP-hydrazones