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Ynol Ethers as Ketene Equivalents in Rhodium-Catalyzed Intermolecular [5 + 2] Cycloaddition Reactions

Paul A. Wender*, Christian Ebner, Brandon D. Fennell, Fuyuhiko Inagaki and Birte Schröder

*Departments of Chemistry and Chemical and Systems Biology, Stanford University, Stanford, California 94305, United States, Email:

P. A. Wender, C. Ebner, B. D. Fennell, F. Inagaki, B. Schröder, Org. Lett., 2017, 19, 5810-5813.

DOI: 10.1021/acs.orglett.7b02765

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Metal-catalyzed, regioselective [5 + 2] cycloadditions of vinylcyclopropanes and electron-rich alkynes (ynol ethers) provide dioxygenated seven-membered rings, a common feature of numerous natural and non-natural targets and building blocks for synthesis. The reactions proceed in high yield at room temperature and tolerate a broad range of functionalities.

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A New and Practical Five-Carbon Component for Metal-Catalyzed [5 + 2] Cycloadditions:  Preparative Scale Syntheses of Substituted Cycloheptenones

P. A. Wender, A. J. Dyckman, C. O. Husfeld, M. J. C. Scanio, Org. Lett., 2000, 2, 1609-1611.

Key Words


ID: J54-Y2017