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

Paul A. Wender, Alaric J. Dyckman, Craig O. Husfeld and Marc J. C. Scanio

*Department of Chemistry, Stanford University, Stanford, California 94305, United States, Email:

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

DOI: 10.1021/ol0058691

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Rh-catalyzed [5 + 2] cycloadditions of 1-(2-methyoxyethoxy)-1-vinylcyclopropane as a five-carbon component to alkynes provide cycloheptenones in many cases in minutes and in very good isolated yields. The procedure is readily conducted on a small or large scale.

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

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

Key Words

cycloheptanones, cycloheptenes, ring expansions

ID: J54-Y2000