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DOI: 10.1055/a-2735-9496
Epoxide Synthesis via Energy-Transfer-Enabled 1,4-Nitrogen Migration
Autor*innen
National Natural Science Foundation of China (nos. 22201179 and 22471168 to H.-M.H.), Supported by State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, the startup funding from ShanghaiTech University.
Dedication
Dedicated to Professor John Murphy on the occasion of his 70th birthday.
Abstract
Epoxides are privileged scaffolds in synthetic chemistry, serving as key precursors for amino alcohols and pharmaceuticals. Traditional strategies to access valuable α-amino epoxides often face limitations in selectivity and require harsh conditions. Inspired by the classic di-π-methane rearrangement, we have developed a visible-light-driven alternative that triggers an unprecedented 1,4-nitrogen migration via an oxa-π,σ-methane rearrangement mechanism. This energy-transfer-catalysis process efficiently converts readily available allylic alcohols into α-amino-substituted epoxides under mild conditions. This method provides a direct and versatile route to these high-value building blocks, bypassing previous synthetic bottlenecks. We describe the discovery and mechanical insights of this new reaction paradigm in detail.
Publikationsverlauf
Eingereicht: 22. September 2025
Angenommen nach Revision: 17. Oktober 2025
Artikel online veröffentlicht:
24. November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
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