Organic Chemistry Portal

Abstracts

Search:

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’Universitą, 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


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.

see article for more examples


see article for more reactions



Key Words

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


ID: J66-Y2002-1710