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Updated: Oct 17, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Application of Allylzinc Reagents as Nucleophiles in Matteson Homologations
Oliver Andler1, Uli Kazmaier1,2
1Organic Chemistry I, Saarland University, Campus Building C4.2, D-66123 Saarbrücken, Germany.
Abstract:
Allylzinc reagents are versatile nucleophiles that can be used in Matteson homologations. The linear substitution products are formed almost exclusively, and excellent E selectivities are observed in reactions of reagents with sterically demanding or aryl substituents on the double bond. The allylated boronic esters obtained can be converted into trifluoroborates or subjected to further homologations. Ozonolysis of the double bond provides aldehydes or ketones, and therefore, allylzinc reagents are useful acetaldehyde or ketone enolate equivalents.
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