,
,
,
and
Beilstein Arch. 2025, 202534. https://doi.org/10.3762/bxiv.2025.34.v1
Published 27 May 2025
The stereoselective electroreductive intramolecular coupling of chiral diimines of aromatic aldehydes with trans-1,2-diaminocyclohexane for the synthesis of enantiopure tetrasubstituted piperazines has been investigated by electrochemical approach. The methodology was successfully developed under both batch and continuous flow conditions, and afforded enantiomerically pure products with complete stereoselectivity. Substrates bearing electron-donating or electron-withdrawing groups on the aromatic rings provided good to excellent yields, indicating that both types of substituents are well tolerated under the reaction conditions. Although modest yields were obtained under flow conditions, the continuous process afforded higher productivities and space-time yields than the batch reactions due to short residence time. This work provides a mild, efficient, and scalable alternative to traditional methods for the synthesis of tetrasubstituted enantiopure piperazines, with potential applications in the preparation of chiral ligands.
Keywords: imino-pinacol coupling; electrosynthesis; chiral piperazines; green chemistry; flow chemistry
| Format: PDF | Size: 4.1 MB | Download |
When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Gazzotti, M.; Medici, F.; Chiroli, V.; Raimondi, L.; Rossi, S.; Benaglia, M. Beilstein Arch. 2025, 202534. doi:10.3762/bxiv.2025.34.v1
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and
Zotero.
© 2025 Gazzotti et al.; licensee Beilstein-Institut.
This is an open access work licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-archives.org/xiv/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this work could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
