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Cycloadditions of 2-nitro 1,3-dienes to enamines. Asymmetric induction and synthesis of unsaturated nitroketones and Diels-Alder adducts via [4+2] heterocycloadditions
Chinchilla,Backvall
, p. 5641 - 5644 (1992)
2-Nitro 1,3-dienes, generated in situ from the corresponding nitroseleno compounds, react with enamines affording [4+2] heterocycloadducts of different stability. With chiral enamines a high asymmetric induction was observed in some cases. Some of the adducts were readily hydrolyzed to unsaturated γ-nitroketones whereas others spontaneously rearranged to Diels-Alder-type carbocycloadducts.
