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Gold(I)-Catalyzed Ring Expansion of Cyclopropanols and Cyclobutanols

Jordan P. Markham, Steven T. Staben and F. Dean Toste*

*Department of Chemistry, University of California, Berkeley, California 94720, Email:

J. P. Markham, S. T. Staben, F. D. Toste, J. Am. Chem. Soc., 2005, 127, 9708-9709.

DOI: 10.1021/ja052831g


A stereospecific gold(I)-catalyzed rearrangement of 1-alkynyl cyclobutanols and cyclopropanols provides alkylidene cycloalkanones. The reaction tolerates terminal alkynes as well as alkyl, aryl, and halo-substitution at the acetylenic position and substituents on the ring.

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Key Words

Ring Expansions, Cyclobutanones

ID: J48-Y2005-2440