Alkene anti-dihydroxylation with malonoyl peroxides

Alamillo-Ferrer, Carla and Davidson, Stuart C. and Rawling, Michael J. and Theodoulou, Natalie H. and Campbell, Matthew and Humphreys, Philip G. and Kennedy, Alan R. and Tomkinson, Nicholas C. O. (2015) Alkene anti-dihydroxylation with malonoyl peroxides. Organic Letters, 17 (20). pp. 5132-5135. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.5b02674)

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Abstract

Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

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• Item metadata

  Item type:	Article
  ID code:	56172
  Dates:	Date Event 16 October 2015 Published 25 September 2015 Accepted
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	15 Apr 2016 13:11
  Last modified:	08 Apr 2024 22:37
  Related URLs:	Related item
  URI:	https://strathprints.strath.ac.uk/id/eprint/56172