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Updated: Jul 28, 2025
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
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Anodic Cyclizations and Umpolung Reactions Involving Imines
Zach Medcalf1, Essence G Redd2, Jaemyeong Oh2
1Department of Chemistry, Washington University in Saint Louis, Saint Louis, Missouri 63130, United States.
Organic Letters
|May 30, 2023
Summary
Anodic cyclization reactions can be channeled into new synthetic pathways by controlling a second electron oxidation step. This study demonstrates a novel method for the asymmetric synthesis of cyclic amines using this approach.
Area of Science:
- Organic electrochemistry
- Synthetic organic chemistry
Background:
- Anodic cyclization reactions are crucial in organic synthesis.
- A key step involves a second electron oxidation downstream of cyclization.
- This step offers potential for controlling reaction pathways.
Purpose of the Study:
- To explore new synthetic pathways using anodic cyclization.
- To demonstrate the utility of a second electron oxidation step in directing reactivity.
- To enable the asymmetric synthesis of cyclic amines via anodic cyclization.
Main Methods:
- Utilizing anodic cyclization with a focus on the second electron oxidation.
- Reversing the typical reactivity of imine groups within the reaction mechanism.
- Developing conditions for asymmetric synthesis.
Main Results:
- Successfully channeled an anodic cyclization reaction down a new synthetic pathway.
- Demonstrated the reversal of imine group reactivity.
- Established a method for the asymmetric synthesis of cyclic amines.
Conclusions:
- The second electron oxidation step is a powerful tool for controlling anodic cyclization pathways.
- This work provides a novel route to asymmetrically synthesized cyclic amines.
- The methodology broadens the scope of electroorganic synthesis.
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