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

Christopher G. Frost; Stephen D. Penrose; Robert Gleave

doi:10.1055/s-0028-1083351

PAPER

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

Christopher G. Frost*^a, Stephen D. Penrose^a, Robert Gleave^b
^a Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, UK
Fax: +44(1225)386231; e-Mail: c.g.frost@bath.ac.uk;
^b Neurology and Gastrointestinal Centre of Excellence for Drug Discovery, GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK

Abstract

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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.

Key words

alkenes - Mannich bases - acrylate derivatives - tandem reactions - aldehydes

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References

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