One-Pot Synthesis of γ-Diketones, γ-Keto Esters, and Conjugated Cyclopentenones from Nitroalkanes

Roberto Ballini*, Luciano Barboni, Giovanna Bosica, Dennis Fiorini

*Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, 62032 Camerino (MC), Italy, Email: roberto.balliniunicam.it

R. Ballini, L . Barboni, G. Bosica, D. Fiorini, Synthesis, 2002, 2725-2728.

DOI: 10.1055/s-2002-35625

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Abstract

Conjugated addition of primary nitroalkanes to α,β-unsaturated ketones or α,β-unsaturated esters, in the presence of two equivalents of DBU, allows the one-pot prepration of γ-diketones or γ-keto esters, respectively. The reaction of 2-aryl-1-nitroethane derivatives with α,β-unsaturated ketones gives cyclopentenones.

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Key Words

nitroalkanes, 1,4-diketones, 1,4-keto esters, cyclopentenones, DBU, Nef Reaction

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ID: J66-Y2002-1710