Journal
ORGANIC LETTERS
Volume 17, Issue 20, Pages 5132-5135Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b02674
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Funding
- EPSRC
- GlaxoSmithKline
- University of Strathclyde
- Engineering and Physical Sciences Research Council [1636131, 1636110, GR/T04113/01] Funding Source: researchfish
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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 degrees 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.
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