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Synthesis 1987; 1987(3): 258-260
DOI: 10.1055/s-1987-27907
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Reaction of Carbanions Derived From α,β-Unsaturated Nitro Compounds With Electrophiles to Give α-Substituted Products

Noboru Ono* , Isami Hamamoto, Akio Kamimura, Aritsune Kaji, Rui Tamura
  • *Department of Chemistry, Faculty of Science, Kyoto University, Kyoto 606, Japan
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Publication Date:
12 September 2002 (online)

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The reaction of α,β-unsaturated nitro compounds with aldehydes or electron deficient olefins, in the presence of a base provides a simple method for the preparation of α-substituted allylic nitro compounds. The initially formed allylic carbanion reacts regioselectively at the position α to the nitro group. The products formed, γ,δ-unsaturated β-nitro alcohols 2 and δ,ε-unsaturated γ-nitro ketones, esters, nitriles, and sulfones 3, can serve as useful synthetic intermediates.