Synthesis p. 242 - 248 (1996)
Update date:2022-09-26
Topics:
Pitacco, Giuliana
Pizzioli, Alessandro
Valentin, Ennio
The morpholino enamine of monoprotected butane-2,3-dione reacts with cyclic and acyclic conjugated nitroalkenes in a Michael-type reaction to yield nitro-substituted α-diketones, after acidic hydrolysis of the mononitroalkylated enamine adducts. Cyclopentanone, hexahydro-1H-pentalen-2-one and octahydro-2H-inden-2-one derivatives are readily obtained by base-catalyzed intramolecular nitroaldol reaction of the acyclic hydrolysis products.
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