Estudio de la reactividad racémica y enantioselectiva del benzoilnitrometano frente a enonas

Abstract

The present work evaluated the reactivity that benzoylnitromethane has against α, β-unsaturated ketones, through additions of Michael and organocatalytic catalysts to obtain an enantiomeric product in greater proportion. The reactions were carried out by reflux using toluene as solvent with different catalysts varying its basicity. After this, reaction was monitored by thin layer chromatography (TLC), using as mobile phase hexane: ethyl ether (1: 4), these compounds were separated by column chromatography. Finally, the products were analyzed by 1 H-NMR, 13 C-NMR and IR. Subsequent the obtained products, the evidence of the products raised in the study, however, it has not been achieved in an enantioselective way barriers due to the steric n present in the reagents used. For this reason, other catalysts with higher basicity values were searched, evidencing that sodium hydroxide was the most effective catalyst of the reaction. Finally, the basicity in the reaction of benzoylnitromethane against the enone had an important role, which favored the inclusion by the carbon of the benzoylitromethane through the formation of its respective enolate, the addition of the ioniminio catalysis was not effected by steric barriers of the enone.