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

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 functionality
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11581/112741
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