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Updated: Feb 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Synthesis of Z- or E-Trisubstituted Allylic Alcohols and Ethers by Kinetically Controlled Cross-Metathesis with a Ru
Chaofan Xu1, Zhenxing Liu1, Sebastian Torker1
1Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.
Abstract:
The first examples of kinetically controlled cross-metathesis reactions that generate Z- or E-trisubstituted alkenes are disclosed. Transformations are catalyzed by ≤6.0 mol % of a Ru catechothiolate complex and afford trisubstituted allylic alcohols and ethers in up to 81% yield and >98% stereoisomeric purity. The method has considerable scope, as olefins containing an alcohol, an aldehyde, an epoxide, a carboxylic acid, or an alkenyl group may be used. Mechanistic models that account for the observed levels and trends in efficiency and stereochemical control are provided, based on DFT studies.
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