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

Christopher G Frost; S D Penrose; R 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, S D Penrose, R Gleave

Department of Chemistry

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

11 Citations (SciVal)

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
Volume	4
DOIs	https://doi.org/10.1055/s-0028-1083351
Publication status	Published - 2009

Keywords

tandem reactions
Mannich bases
alkenes
acrylate derivatives

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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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AU - Penrose, S D

AU - Gleave, R

PY - 2009

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N2 - 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.

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 - tandem reactions

KW - Mannich bases

KW - alkenes

KW - acrylate derivatives

UR - https://www.scopus.com/pages/publications/63849160331

UR - http://dx.doi.org/10.1055/s-0028-1083351

U2 - 10.1055/s-0028-1083351

DO - 10.1055/s-0028-1083351

M3 - Article

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EP - 635

JO - Synthesis

JF - Synthesis

ER -

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

Abstract

Keywords

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