UNPRECEDENTED GAMMA-SELECTIVE MICHAEL ADDITION OF TIN(II) DIENOLATES TO ACYCLIC α,β-UNSATURATED KETONES

Tin(II) dienolates were found to react exclusively at the gamma carbon with acyclic α,β-unsaturated ketones in the Michael sense. Either acyclic 1,7-diketones or 2-cyclohexenol derivatives could be obtained in moderate to excellent yields by appropriate choice of reaction parameters. Moreover, in the latter case, only a single cyclohexenol adduct was afforded.