Synthesis, Stability and Diels‐Alder Reactions of Methyl 2‐Oxobut‐3‐enoate

Bo Michael Jessen, Esben Taarning, Robert Madsen*

*Corresponding author for this work

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Methyl vinyl glycolate (MVG, methyl 2‐hydroxybut‐3‐enoate) is a new biobased platform chemical, which is available by degradation of carbohydrates. In the present work, the oxidation of MVG to methyl 2‐oxobut‐3‐enoate has been investigated and a procedure developed with the Dess‐Martin periodinane. Methyl 2‐oxobut‐3‐enoate has not been characterized before and is stable for days at −18 °C, but slowly dimerizes by an unusual hetero‐Diels‐Alder reaction at room temperature. Therefore, the reactivity of methyl 2‐oxobut‐3‐enoate in the normal Diels‐Alder reaction with 1,3‐dienes has been investigated and a one‐pot procedure developed where MVG is first oxidized with the Dess‐Martin periodinane followed by addition of the 1,3‐diene. A number of different 1,3‐dienes can take part in the cycloaddition to afford the functionalized cyclohexene products in moderate‐to‐good yields.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Issue number29
Pages (from-to)4049-4053
Number of pages5
Publication statusPublished - 2021


  • Cycloaddition
  • Enones
  • Oxidation
  • Platform chemicals
  • Synthetic methods


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