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A Practical Synthesis of α-Substituted tert-Butyl Acrylates from Meldrum's Acid and Aldehydes

Christopher G. Frost*, Stephen D. Penrose, Robert Gleave

*Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK, Email:

C. G. Frost, S. D. Penrose, R. Gleave, Synthesis, 2009, 627-635.

DOI: 10.1055/s-0028-1083351


An expeditious synthesis of α-substituted tert-butyl acrylates from commercially available aldehydes and Meldrum's acid includes 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.

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Key Words

active methylene compounds (alkylation, benzylation), sodium borohydride, terminal olefins, α,β-unsaturated esters

ID: J66-Y2009-0490