Reaction of Carbanions Derived From α,β-Unsaturated Nitro Compounds With Electrophiles to Give α-Substituted Products
- 1 January 1987
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1987 (03) , 258-260
- https://doi.org/10.1055/s-1987-27907
Abstract
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.Keywords
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