Palladium-Catalyzed [1,3]-O-to-C Rearrangement of Pyrans toward Functionalized Cyclohexanones

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• 作者：Julien C. R. Brioche ; Thomas A. Barker ; David J. Whatrup ; Michael D. Barker ; Joseph P. A. Harrity
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：November 5, 2010
• 年：2010
• 卷：12
• 期：21
• 页码：4832-4835
• 全文大小：193K
• 年卷期：v.12,no.21(November 5, 2010)
• ISSN：1523-7052

文摘

Functionalized cyclohexanones are prepared from cyclic enol ethers via a Pd-catalyzed [1,3]-O-to-C rearrangement reaction. α-Arylketones are generated with excellent diastereocontrol when basic phosphine ligands are used. In contrast, a Lewis acid is required to promote the rearrangement of the alkyl-substituted enol ether systems.