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 re...

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Bibliographic Details
Published in:Organic letters 2020-11, Vol.22 (22), p.9075-9080
Main Authors: Zuckerman, Dylan S, Woerpel, K. A
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03439