An expeditious synthesis of α-substituted tert-butyl acrylates from commercially available aldehydes and Meldrum's acid has been established. The method benefits from a telescoped condensation-reduction sequence to afford 5-monosubstituted Meldrum's acid derivatives followed by a Mannich-type reaction triggered by a rapid cycloreversion of the dioxinone ring on heating with tert-butyl alcohol.
- tandem reactions
- Mannich bases
- acrylate derivatives
Frost, C. G., Penrose, S. D., & Gleave, R. (2009). A Practical Synthesis of α-Substituted tert-Butyl Acrylates from Meldrum's Acid and Aldehydes. Synthesis, 4, 627-635. https://doi.org/10.1055/s-0028-1083351