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

被引：10

作者：

Frost, Christopher G. ^{[1
]}

Penrose, Stephen D. ^{[1
]}

Gleave, Robert ^{[2
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] GlaxoSmithKline, Neurol & Gastrointestinal Ctr Excellence Drug Dis, Harlow CM19 5AW, Essex, England

来源：

SYNTHESIS-STUTTGART | 2009年 / 04期

基金：

英国工程与自然科学研究理事会;

关键词：

alkenes; Mannich bases; acrylate derivatives; tandem reactions; aldehydes; BAYLIS-HILLMAN REACTION; PART; 2; TANDEM; WATER; STRATEGIES;

D O I：

10.1055/s-0028-1083351

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expeditious synthesis of alpha-substituted terf-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 or the dioxinone ring on heating with tert-butyl alcohol.

引用

页码：627 / 635

页数：9

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