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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 | 2020 Nov

REPOSITORIES: biostudies-literature

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

Zuckerman Dylan S DS Woerpel K A KA

Organic letters 20201103 22

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 natura ...[more]

PMID: 33141576

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