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Updated: Apr 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides
Bardia Soltanzadeh1, Arvind Jaganathan2, Richard J Staples1
1Department of Chemistry, Michigan State University, E. Lansing, MI 48824 (USA).
Abstract:
An organocatalytic and highly regio-, diastereo-, and enantioselective intermolecular haloetherification and haloesterification reaction of allyl amides is reported. A variety of alkene substituents and substitution patterns are compatible with this chemistry. Notably, electronically unbiased alkene substrates exhibit exquisite regio- and diastereoselectivity for the title transformation. We also demonstrate that the same catalytic system can be used in both chlorination and bromination reactions of allyl amides with a variety of nucleophiles with little or no modification.
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