Related Experiment Video
Updated: Aug 18, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nickel-catalyzed intramolecular homoallylation of omega-dienyl aldehyde
K Shibata1, M Kimura, M Shimizu
1Department of Applied Chemistry, Faculty of Engineering, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
Abstract:
[reaction: see text] In the presence of a catalytic amount of Ni(acac)(2), Et(3)B and Et(2)Zn nicely promote a reductive homoallylic cyclization of omega-dienyl aldehydes and provide 2-allylcyclopentanols and -cyclohexanols with high stereoselectivity in excellent yield. The reaction requires only two kinds of commercially available, inexpensive reagents, Ni(acac)(2) and Et(2)Zn or Et(3)B, and completes at room temperature within 30 min with Et(2)Zn and 1-2 days with Et(3)B. No ligand additives (e.g., phosphine, nitrogen compounds) are required.
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
α-Alkylation of Ketones via Enolate Ions
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation

