Alkene anti-dihydroxylation with malonoyl peroxides
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: https://orcid.org/0000-0003-3607-846X, Davidson, Stuart C. ORCID: https://orcid.org/0000-0003-2202-2625, Rawling, Michael J., Theodoulou, Natalie H., Campbell, Matthew ORCID: https://orcid.org/0000-0002-6003-7257, Humphreys, Philip G., Kennedy, Alan R. ORCID: https://orcid.org/0000-0003-3652-6015 and Tomkinson, Nicholas C. O. ORCID: https://orcid.org/0000-0002-5509-0133;-
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Item type: Article ID code: 56172 Dates: DateEvent16 October 2015Published25 September 2015AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry Depositing user: Pure Administrator Date deposited: 15 Apr 2016 13:11 Last modified: 31 Aug 2024 00:52 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/56172