Synthesis 1994; 1994(7): 723-726
DOI: 10.1055/s-1994-25557
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Chemoselective Conversion of Conjugated Nitroalkenes into Ketones by Sodium Borohydride-Hydrogen Peroxide: A New Synthesis of 4-Oxoalkanoic Acids, Dihydrojasmone and (±)-exo-Brevicomin

Roberto Ballini* , Giovanna Bosica
  • *Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, I-62032 Camerino, Italy
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Publikationsverlauf

Publikationsdatum:
17. September 2002 (online)

A new, simple, cheap, and practical procedure for the direct transformation of α,β-unsaturated nitroalkenes into ketones has been realized by the NaBH4/H2O2 system. By this method, other functional groups such as C-C double bonds, ketals or aromatic nitro groups were preserved. Application of this methodology to the preparation of 4-oxoalkanoic acids, dihydrojasmone, and (±)-exo-brevicomin is also reported.