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DOI: 10.1055/a-2505-2699
Reductive Ring Opening of Cyclic Amines: Pyrrolidines and Beyond
This work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant Numbers JP21H05213 (Digi-TOS) to J.Y., JP23K13752 to E.O.), the Uehara Memorial Foundation (to E.O.), and the Satomi Foundation (to E.O.). This work was partly supported by the Japan Science and Technology Agency (JST) Exploratory Research for Advanced Technology (ERATO, Grant Number JPMJER1901 to J.Y.).
Abstract
The reductive ring opening of cyclic amines is a powerful strategy for transforming cyclic structures into entirely different molecular frameworks, with significant potential application in synthetic and medicinal chemistry. Previously reported methods have been primarily limited to highly strained substrates such as aziridines and azetidines. In this study, we report a novel approach for generating carbon-centered radicals upon ring opening from less strained cyclic amines, particularly pyrrolidines, using Lewis acid and photoredox catalysis. Notably, while still in its early stages, this method shows potential applicability to larger rings, such as six- and seven-membered systems. Here, we detail the development, scope, and potential of this method, demonstrating efficient and selective reactions of a range of cyclic amines.
1 Introduction
2 Recent Examples of Reductive Ring Opening of Pyrrolidines
3 Our Working Hypothesis and Ring Opening of Pyrrolidines
4 Conclusion
Publikationsverlauf
Eingereicht: 27. November 2024
Angenommen nach Revision: 17. Dezember 2024
Accepted Manuscript online:
17. Dezember 2024
Artikel online veröffentlicht:
09. April 2025
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