Redox Properties of Catalytically Generated Iminium Ions From α,β‐Unsaturated Aldehydes and Chiral Secondary Amines
Fuente:
Wiley Open Access
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Artículo Open Access |
| Published: |
Wiley
2026
|
| Subjects: | |
| Online Access: | |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1867006912497713152 |
|---|---|
| author | Martí Gisbert Paula Rodríguez Xavier Companyó |
| author_facet | Martí Gisbert Paula Rodríguez Xavier Companyó Martí Gisbert Paula Rodríguez Xavier Companyó |
| collection | Wiley Open Access |
| contents | Redox Properties of Catalytically Generated Iminium Ions From α,β‐Unsaturated Aldehydes and Chiral Secondary Amines Martí Gisbert Paula Rodríguez Xavier Companyó European Journal of Organic Chemistry Chiral iminium ions are key catalytic intermediates in aminocatalysis, enabling a wide range of enantioselective transformations. Yet, a systematic study of how their electrochemical properties vary as a function of the different reaction components has remained elusive, largely due to their transient nature and inherent instability. Herein we show a general protocol for the catalytic generation and in situ cyclic voltammetric characterisation of over 50 chiral iminium ions. This analysis reveals how the catalyst electronics, aldehyde nature and substitution, and the solvent environment governs their reduction potential. This electrochemical mapping provides predictive insights into iminium ion reactivity via single‐electron transfer, laying the groundwork for the rational design of novel radical‐based asymmetric transformations. 10.1002/ejoc.70549 http://creativecommons.org/licenses/by/4.0/ |
| doi_str_mv | 10.1002/ejoc.70549 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_ejoc_70549 |
| institution | Wiley Open Access |
| license_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| publishDate | 2026 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Redox Properties of Catalytically Generated Iminium Ions From α,β‐Unsaturated Aldehydes and Chiral Secondary Amines Martí Gisbert Paula Rodríguez Xavier Companyó European Journal of Organic Chemistry Redox Properties of Catalytically Generated Iminium Ions From α,β‐Unsaturated Aldehydes and Chiral Secondary Amines Martí Gisbert Paula Rodríguez Xavier Companyó European Journal of Organic Chemistry Chiral iminium ions are key catalytic intermediates in aminocatalysis, enabling a wide range of enantioselective transformations. Yet, a systematic study of how their electrochemical properties vary as a function of the different reaction components has remained elusive, largely due to their transient nature and inherent instability. Herein we show a general protocol for the catalytic generation and in situ cyclic voltammetric characterisation of over 50 chiral iminium ions. This analysis reveals how the catalyst electronics, aldehyde nature and substitution, and the solvent environment governs their reduction potential. This electrochemical mapping provides predictive insights into iminium ion reactivity via single‐electron transfer, laying the groundwork for the rational design of novel radical‐based asymmetric transformations. 10.1002/ejoc.70549 http://creativecommons.org/licenses/by/4.0/ |
| title | Redox Properties of Catalytically Generated Iminium Ions From α,β‐Unsaturated Aldehydes and Chiral Secondary Amines |
| topic | European Journal of Organic Chemistry |
| url | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.70549 |