Aldol–Tishchenko reaction

The Aldol–Tishchenko reaction is a tandem reaction involving an aldol reaction and a Tishchenko reaction.

In organic synthesis, it is a method to convert aldehydes and ketones into 1,3-hydroxyl compounds.

The reaction sequence in many examples starts from conversion of a ketone into an enolate by action of lithium diisopropylamide (LDA), to which a suitable aldehyde is added.

The resulting mono-ester diol is then converted into the diol by a hydrolysis step.

With both the acetyl trimethylsilane[1] and propiophenone[2] as reactants, the diol is obtained as a pure diastereoisomer.