Alkene syn- and anti-oxyamination with malonoyl peroxides

Jonathan M. Curle, Marina C. Perieteanu, Philip G. Humphreys, Alan R. Kennedy, Nick C. O. Tomkinson

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)
17 Downloads (Pure)


Malonoyl peroxide [6] is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of [6] and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R3 = CO2Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.
Original languageEnglish
Pages (from-to)1659-1664
Number of pages6
JournalOrganic Letters
Issue number4
Early online date30 Jan 2020
Publication statusPublished - 21 Feb 2020


  • organic chemistry
  • Malonoyl peroxide
  • alkenes
  • alkene oxyamination


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