Tetrahedron

Horner-Wadsworth-Emmons olefination of nonstabilized phosphonates. A new synthetic approach to β, γ-unsaturated amides

T Janecki, R Bodalski, G Bujacz

文献索引：Janecki; Janecki, Tomasz; Bodalski; Bodalski, Ryszard; Wieczorek; Wieczorek, Michakl; Bujacz; Bujacz, Grzegorz Tetrahedron, 1995 , vol. 51, # 6 p. 1721 - 1740

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被引用次数: 15

摘要

Aminolysis of readily accessible β-diethoxyphosphonyl-γ-butyrolactones 5 and 22 provides a convenient entry to (E)-β, γ-unsaturated amides 8 and 24 respectively. The key step of the aminolysis involves elimination of diethoxyphosporic acid from the corresponding β- hydroxyalkylphosphonates 7 and 23. Stereochemistry of the amides 8 and 24 results from their consecutive base catalyzed isomerization.