Synthesis of enantiopure triols from racemic Baylis−Hillman adducts using a diastereoselective peroxidation reaction

K. A. Woerpel, Dylan S. Zuckerman

Research output: Contribution to journalArticlepeer-review

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 languageEnglish (US)
Pages (from-to)9075-9080
Number of pages6
JournalOrganic Letters
Volume22
Issue number22
DOIs
StatePublished - Nov 20 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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