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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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.