Alkene anti-dihydroxylation with malonoyl peroxides

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Alamillo-Ferrer, Carla and Davidson, Stuart C. and Rawling, Michael J. and Theodoulou, Natalie H. and Campbell, Matthew and Humphreys, Philip G. and Kennedy, Alan R. and Tomkinson, Nicholas C. O. (2015) Alkene anti-dihydroxylation with malonoyl peroxides. Organic Letters, 17 (20). pp. 5132-5135. ISSN 1523-7060 (https://doi.org/10.1021/acs.orglett.5b02674)

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Abstract

Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

ORCID iDs

Alamillo-Ferrer, Carla ORCID logoORCID: https://orcid.org/0000-0003-3607-846X, Davidson, Stuart C. ORCID logoORCID: https://orcid.org/0000-0003-2202-2625, Rawling, Michael J., Theodoulou, Natalie H., Campbell, Matthew ORCID logoORCID: https://orcid.org/0000-0002-6003-7257, Humphreys, Philip G., Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
CORE (COnnecting REpositories)