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

ABSTRACT: 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.

SUBMITTER: Zuckerman DS 

PROVIDER: S-EPMC7680403 | biostudies-literature |

REPOSITORIES: biostudies-literature