LTA-mediated β-oxidative decarbonylation of homoallylic alcohols

ORGN 169

Marcelo D. Preite, Andrés E. Pérez Carvajal, and Mauricio A. Cuellar. Departamento de Química Orgánica, Pontificia Universidad Católica de Chile, Facultad de Química, Vicuña Mackenna 4860, Santiago, Chile
Recently, we found that when an homoallylic alcohol is heated in the presence of lead tetraacetate (LTA) in a refluxing inert solvent, a β-oxidative decarbonylation occurs, to give a dehomologated allylic acetate in high yield. This reaction seems to be of general use, very easy to run in any inert solvent, at room or somewhat higher temperature, showing an inverse relationship between reaction time and temperature.