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.
Creators(s): |
Curle, Jonathan M., Perieteanu, Marina C., Humphreys, Philip G., Kennedy, Alan R. ![]() ![]() | Item type: | Article |
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ID code: | 71376 |
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: | 15 Jan 2021 04:21 |
URI: | https://strathprints.strath.ac.uk/id/eprint/71376 |
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