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.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry