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

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• 作者：Jordan P. Markham ; Steven T. Staben ; and F. Dean Toste
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：July 13, 2005
• 年：2005
• 卷：127
• 期：27
• 页码：9708 - 9709
• 全文大小：70K
• 年卷期：v.127,no.27(July 13, 2005)
• ISSN：1520-5126

文摘

The rearrangement of 1-alkynyl cyclobutanols and cyclopropanols to alkylidene cycloalkanones catalyzed by cationic triarylphosphine gold(I) complexes is described. The reaction tolerates terminal alkynes as well as alkyl, aryl, and halo-substitution at the acetylenic position and stereoselectively provides a single olefin isomer. The gold(I)-catalyzed rearrangement is stereospecific with regard to substituents on the ring, thus providing a practical method for the stereoselective synthesis of highly substituted cyclopentanones from cyclopropanols. The reaction stereoselectively provides a single olefin isomer and is stereospecific with regard to substituents on the ring via sequential gold(I)-catalyzed ring expansion reactions.