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Updated: Jun 22, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Stereoselective cross-coupling between allylic alcohols and aldimines
Ivan L Lysenko1, Hyung Goo Lee, Jin Kun Cha
1Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
This study introduces a new cross-coupling reaction for stereoselective allylation of imines using allylic alcohols. The method offers a simple, enantioselective route to functionalized homoallylic amines without preformed organometallic reagents.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Allylic alcohols are versatile building blocks.
- Stereoselective synthesis of homoallylic amines is crucial in medicinal chemistry.
Purpose of the Study:
- To develop an operationally simple and enantioselective method for allylation of imines.
- To utilize allylic alcohols directly as allylating reagents.
Main Methods:
- Cross-coupling reaction between allylic alcohols and imines.
- Stereoselective synthesis.
Main Results:
- Successful stereoselective allylation of aromatic and aliphatic imines.
- Enantioselective synthesis of functionalized homoallylic amines.
- Direct use of allylic alcohols without prederivatization.
Conclusions:
- The developed method provides efficient access to valuable homoallylic amine scaffolds.
- This approach avoids the need for preformed organometallic reagents or activated imine derivatives, simplifying the synthetic process.
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