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

Alamillo-Ferrer, Carla and Karabourniotis-Sotti, Marianna and Kennedy, Alan R. and Campbell, Matthew and Tomkinson, Nicholas C. O. (2016) Alkene dioxygenation with malonoyl peroxides : synthesis of ɣ-lactones, isobenzofuranones and tetrahydrofurans. Organic Letters. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.6b01253)

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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.

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• Item metadata

  Item type:	Article
  ID code:	56646
  Dates:	Date Event 17 June 2016 Published 17 June 2016 Published Online 12 June 2016 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	13 Jun 2016 14:15
  Last modified:	09 Apr 2024 08:24
  Related URLs:	Journal or Publication
  URI:	https://strathprints.strath.ac.uk/id/eprint/56646