Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 41, Pages 14409-14411Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja1066674
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Funding
- Leverhulme Trust
- EPSRC
- GlaxoSmithKline
- Engineering and Physical Sciences Research Council [GR/T04113/01] Funding Source: researchfish
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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 degrees 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.
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