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Updated: Jun 12, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Chromium-catalyzed homoaldol equivalent reaction employing a nucleophilic propenyl acetate
Jun Yong Kang1, Brian T Connell
1Texas A&M University, Department of Chemistry, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Abstract:
A scalable, highly regioselective chromium-catalyzed homoaldol equivalent reaction employing 3-bromopropenyl acetate as a masked homoenolate nucleophile in additions to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes under mild Cr/Mn redox conditions in good to excellent yields is reported. The resulting vinyl acetate-containing adducts are easily hydrolyzed with mild base to provide formal homoaldol adducts, or transformed to other more functionalized products by stereoselective transformations including epoxidation and cyclopropanation.
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