Metal-free dihydroxylation of alkenes using cyclobutane malonoyl peroxide

Nick Tomkinson, Kevin M Jones

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Abstract

Cyclobutane malonoyl peroxide (7), prepared in a single step from the commercially available diacid 6, is an effective reagent for the dihydroxylation of alkenes. Reaction of a chloroform solution of 7 with an alkene in the presence of one equivalent of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (30–84%). With 1,2-disubstituted alkenes the reaction proceeds with syn-selectivity (3:1–>50:1). A mechanism consistent with experimental findings is proposed which is supported by deuterium and oxygen labeling studies and explains the stereoselectivity observed. Alternative reaction pathways that are dependent on the structure of the starting alkene are also described leading to the synthesis of allylic alcohols and γ-lactones.
Original languageEnglish
Pages (from-to)921-928
Number of pages8
JournalJournal of Organic Chemistry
Volume77
Issue number2
DOIs
Publication statusPublished - Jan 2012

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Keywords

  • dihydroxylation
  • alkenes
  • cyclobutane malonoyl peroxide

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