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

Christopher G Frost, S D Penrose, R Gleave

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8 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)627-635
Number of pages9
JournalSynthesis
Volume4
DOIs
Publication statusPublished - 2009

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Keywords

  • tandem reactions
  • Mannich bases
  • alkenes
  • acrylate derivatives

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