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Synthesis 2009(4): 627-635  
DOI: 10.1055/s-0028-1083351
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Christopher G. Frost*a, Stephen D. Penrosea, Robert Gleaveb
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
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Publikationsverlauf

Received 29 August 2008
Publikationsdatum:
02. Februar 2009 (online)

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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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