Alkene anti-dihydroxylation with malonoyl peroxides

Carla Alamillo-Ferrer, Stuart C. Davidson, Michael J. Rawling, Natalie H. Theodoulou, Matthew Campbell, Philip G. Humphreys, Alan R. Kennedy, Nicholas C. O. Tomkinson

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66 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)5132-5135
Number of pages4
JournalOrganic Letters
Volume17
Issue number20
DOIs
Publication statusPublished - 16 Oct 2015

Keywords

  • anti-Dihydroxylation
  • Malonoyl Peroxides
  • alkenes
  • alkaline hydrolysis

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  • Cite this

    Alamillo-Ferrer, C., Davidson, S. C., Rawling, M. J., Theodoulou, N. H., Campbell, M., Humphreys, P. G., ... Tomkinson, N. C. O. (2015). Alkene anti-dihydroxylation with malonoyl peroxides. Organic Letters, 17(20), 5132-5135. https://doi.org/10.1021/acs.orglett.5b02674