Skip to content
qorganica.es qorganica.comOrganic Chemistry made transparent Course map Español

Robinson Annulation

The synthetic sequence of a Michael (conjugate) addition followed by an intramolecular aldol condensation, leading to a cyclohexenone, is called the Robinson annulation.

Robinson annulation▶ Watch the video on YouTube
Robinson annulation, first step: the enolate attacks an α,β-unsaturated ketone in a conjugate fashion

In the first step, the enolate of an aldehyde, a ketone or a dicarbonyl compound attacks an α,β-unsaturated ketone in a conjugate fashion.

Robinson annulation, second step: intramolecular aldol condensation and dehydration to a cyclohexenone

In the second step, the enolate formed in the conjugate addition attacks intramolecularly the carbonyl group that started the reaction. The most stable ring (six-membered) is formed, and a cyclohexenone is obtained after the dehydration typical of aldol condensations.

The reaction is named after Robert Robinson, who described it in 1935.