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
bath.ac.uk
C. G. Frost, S. D. Penrose, R. Gleave, Synthesis, 2009, 627-635.
DOI: 10.1055/s-0028-1083351
Abstract
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.
see article for more examples
Key Words
active methylene compounds (alkylation, benzylation), sodium borohydride, terminal olefins, α,β-unsaturated esters
ID: J66-Y2009-0490
