Journal article
Asymmetric reductive arylation and alkenylation to access S-chirogenic sulfinamides
- Abstract:
- The study of the stereochemistry of organic sulfur compounds has been ongoing for over a century, with S-chirogenic pharmacophores playing an essential role in drug discovery within bioscience and medicinal chemistry. Traditionally, the synthesis of sulfinamides featuring stereogenic sulfur(IV) centers involves a complex, multistep process that often depends on chiral auxiliaries or kinetic resolution. Here, we introduce an effective and versatile method for synthesizing diverse classes of S-chirogenic sulfinamides through selective aryl and alkenyl addition to sulfinylamines. This process is catalysed by a chiral nickel or cobalt complex under reductive conditions, and eliminating the need for preformed organometallic reagents. The method facilitates the incorporation of a diverse array of aryl and alkenyl halides at the sulfur position, enabling their integration into various biologically significant sulfur pharmacophores. Our detailed mechanistic investigations and density functional theory calculations provide insights into the reaction pathway, particularly highlighting the enantiocontrol mode during addition process.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 1.3MB, Terms of use)
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- Publisher copy:
- 10.1038/s41467-025-57471-9
Authors
- Publisher:
- Springer Nature
- Journal:
- Nature Communications More from this journal
- Volume:
- 16
- Issue:
- 1
- Article number:
- 2547
- Publication date:
- 2025-03-15
- Acceptance date:
- 2025-02-24
- DOI:
- EISSN:
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2041-1723
- Language:
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English
- Pubs id:
-
2094677
- Local pid:
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pubs:2094677
- Source identifiers:
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2775010
- Deposit date:
-
2025-03-15
Terms of use
- Copyright holder:
- Fang et al.
- Copyright date:
- 2025
- Rights statement:
- © The Author(s) 2025. Open Access. This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License, which permits any non-commercial use, sharing, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if you modified the licensed material. You do not have permission under this licence to share adapted material derived from this article or parts of it. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder.
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