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.
Original language | English (US) |
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Pages (from-to) | 9075-9080 |
Number of pages | 6 |
Journal | Organic Letters |
Volume | 22 |
Issue number | 22 |
DOIs | |
State | Published - Nov 20 2020 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry