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

A practical synthesis of α-substituted tert-butyl acrylates from meldrum's acid and aldehydes

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

Chemistry

Research output: Contribution to journal › Article › peer-review

11 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 language	English
Pages (from-to)	627-635
Number of pages	9
Journal	Synthesis
Issue number	4
DOIs	https://doi.org/10.1055/s-0028-1083351
Publication status	Published - 2009

Keywords

Acrylate derivatives
Aldehydes
Alkenes
Mannich bases
Tandem reactions

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10.1055/s-0028-1083351

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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.",

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AB - 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.

KW - Acrylate derivatives

KW - Aldehydes

KW - Alkenes

KW - Mannich bases

KW - Tandem reactions

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A practical synthesis of α-substituted tert-butyl acrylates from meldrum's acid and aldehydes

Abstract

Keywords

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