Alkene syn- and anti-oxyamination with malonoyl peroxides

Curle, Jonathan M. and Perieteanu, Marina C. and Humphreys, Philip G. and Kennedy, Alan R. and Tomkinson, Nick C. O. (2020) Alkene syn- and anti-oxyamination with malonoyl peroxides. Organic Letters, 22 (4). pp. 1659-1664. ISSN 1523-7060

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    Abstract

    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.

    ORCID iDs

    Curle, Jonathan M., Perieteanu, Marina C., Humphreys, Philip G., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nick C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
    • Item type:Article
      ID code:71376
      Dates:
      Date
      Event
      21 February 2020
      Published
      30 January 2020
      Published Online
      23 January 2020
      Accepted
      Keywords:organic chemistry, Malonoyl peroxide, alkenes, alkene oxyamination, Physical and theoretical chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry
      Subjects:Science > Chemistry > Physical and theoretical chemistry
      Department:Faculty of Science > Pure and Applied Chemistry
      Depositing user: Pure Administrator
      Date deposited:06 Feb 2020 16:03
      Last modified:23 Sep 2021 07:37
      URI:https://strathprints.strath.ac.uk/id/eprint/71376
    CORE (COnnecting REpositories)