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

Bo Michael Jessen, Esben Taarning, Robert Madsen*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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
Volume2021
Issue number29
Pages (from-to)4049-4053
Number of pages5
ISSN1434-193X
DOIs
Publication statusPublished - 2021

Keywords

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

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