Synthesis of Enantiopure Triols from Racemic Baylis–Hillman Adducts Using a Diastereoselective Peroxidation Reaction

Using a chiral (−)-menthone auxiliary, enantiopure cyclic derivatives of Baylis–Hillman adducts were synthesized. A diastereoselective peroxidation reaction was used to introduce an oxygen atom and establish another stereocenter. The resulting products could be elaborated by employing a one-flask reduction–acetylation protocol followed by a diastereoselective nucleophilic substitution reaction. Removal of the (−)-menthone auxiliary provided an enantiopure triol with a structure related to naturally occurring polyols.