Cerium-Catalyzed Formal Cycloaddition of Cycloalkanols with Alkenes through Dual Photoexcitation

We describe a synergistic utilization of cerium photocatalysis and photoinduced electron transfer catalysis that enables an atom- and step-economical ring expansion of readily available cycloalkanols. This operationally simple protocol provides rapid access to privileged and synthetically challengin...

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Veröffentlicht in:Journal of the American Chemical Society 2018-10, Vol.140 (42), p.13580-13585
Hauptverfasser: Hu, Anhua, Chen, Yilin, Guo, Jing-Jing, Yu, Na, An, Qing, Zuo, Zhiwei
Format: Artikel
Sprache:eng
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Zusammenfassung:We describe a synergistic utilization of cerium photocatalysis and photoinduced electron transfer catalysis that enables an atom- and step-economical ring expansion of readily available cycloalkanols. This operationally simple protocol provides rapid access to privileged and synthetically challenging bridged lactones. The mild catalytic manifold has been adapted to continuous flow for scale-up applications and employed for the concise synthesis of polycyclic core of nepalactones.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b08781