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Updated: Jun 9, 2026
06:46
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper-catalyzed olefin aminoacetoxylation
Danny E Mancheno1, Aaron R Thornton, Armin H Stoll
1Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Organic Letters
|August 26, 2010
Summary
A novel catalyst system efficiently forms piperdines from olefins. This new method works with challenging terminal and disubstituted olefins, outperforming older palladium and copper catalysts.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Intramolecular olefin aminoacetoxylation is a key transformation in organic synthesis.
- Existing palladium- and copper-catalyzed systems have limitations in substrate scope and reactivity.
Purpose of the Study:
- To develop a new catalyst system for intramolecular olefin aminoacetoxylation.
- To broaden the substrate scope, including terminal and disubstituted olefins.
Main Methods:
- Development of a novel catalyst system.
- Optimization of reaction conditions for piperidine formation.
- Testing the catalyst with various terminal and disubstituted olefin substrates.
Main Results:
- The new catalyst system promotes piperidine formation with terminal olefin substrates.
- Cyclization is successfully induced with traditionally less reactive disubstituted olefins.
- The developed method offers an advantage over existing palladium- and copper-catalyzed systems.
Conclusions:
- A new, effective catalyst system for intramolecular olefin aminoacetoxylation has been established.
- This system expands the utility of this reaction for synthesizing piperidine derivatives.
- The findings present a valuable advancement in synthetic organic chemistry.
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