Alkene syn dihydroxylation with malonoyl peroxides

Griffith, James C and Jones, Kevin M and Picon, Sylvain and Rawling, Michael J and Kariuki, Benson M and Campbell, Matthew and Tomkinson, Nicholas C. O. (2010) Alkene syn dihydroxylation with malonoyl peroxides. Journal of the American Chemical Society, 132 (41). pp. 14409-14411. ISSN 0002-7863 (https://doi.org/10.1021/ja1066674)

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Abstract

Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.

  • Item type:Article
    ID code:33051
    Dates:
    Date
    Event
    20 October 2010
    Published
    24 September 2010
    Published Online
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:30 Aug 2011 08:57
    Last modified:08 Apr 2024 19:21
    URI:https://strathprints.strath.ac.uk/id/eprint/33051
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