Bringing together beta-nitroalkanols and cis-3-hexen-2,5dione. in the presence of DBU as base and in acetonitrile as solvent, we achieved a one-pot diastereoselective synthesis of dihydropyranol derivatives. The nature of the latter compounds is consistent with the initial formation of a Michael adduct, followed by base-promoted elimination of nitrous acid leading to an allylic alcohol, which, finally, cyclises diastereoselectively to form a hemi-ketal functionality
Anionic domino process for the one-pot, diastereoselective synthesis of dihydropyranols from β-nitroalcohols
BALLINI, Roberto;BARBONI, Luciano;FIORINI, Dennis;PALMIERI, Alessandro
2004-01-01
Abstract
Bringing together beta-nitroalkanols and cis-3-hexen-2,5dione. in the presence of DBU as base and in acetonitrile as solvent, we achieved a one-pot diastereoselective synthesis of dihydropyranol derivatives. The nature of the latter compounds is consistent with the initial formation of a Michael adduct, followed by base-promoted elimination of nitrous acid leading to an allylic alcohol, which, finally, cyclises diastereoselectively to form a hemi-ketal functionalityFile in questo prodotto:
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