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Updated: Jul 19, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Reusable catalysts for the asymmetric Diels-Alder reaction
Guillaume Chollet1, Marie-George Guillerez, Emmanuelle Schulz
1Equipe de Catalyse Moléculaire, ICMMO, UMR 8182, Université Paris-Sud, 91405 Orsay, France.
Abstract:
A new method for recycling chiral bis(oxazoline)-copper complexes is described based on the formation of charge-transfer complexes, their subsequent precipitation, and reuse after addition of new substrates. The conditions to perform this procedure were optimized in the presence of three bis(oxazoline)-based ligands. When associated with copper salts, these ligands efficiently catalyzed the Diels-Alder reaction between cyclopentadiene and alpha,beta-unsaturated acyloxazolidinones. These catalysts were successfully recycled up to ten times while maintaining their high activities and enantioselectivities.
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