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 language | English |
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Journal | European Journal of Organic Chemistry |
Volume | 2021 |
Issue number | 29 |
Pages (from-to) | 4049-4053 |
Number of pages | 5 |
ISSN | 1434-193X |
DOIs | |
Publication status | Published - 2021 |
Keywords
- Cycloaddition
- Enones
- Oxidation
- Platform chemicals
- Synthetic methods