Alkene dioxygenation with malonoyl peroxides: synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans

Carla Alamillo-Ferrer, Marianna Karabourniotis-Sotti, Alan R. Kennedy, Matthew Campbell, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)
18 Downloads (Pure)

Abstract

Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, ɣ-lactones and isobenzofuranones in 44–82% yield and up to 27:1 trans-selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.
Original languageEnglish
Number of pages5
JournalOrganic Letters
Early online date17 Jun 2016
DOIs
Publication statusE-pub ahead of print - 17 Jun 2016

Keywords

  • saturated oxygen heterocycles
  • homoallylic alcohols
  • carboxylic acids

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