Zinc-Mediated C-C Bond Sigmatropic Rearrangement: A New and Efficient Methodology for the Synthesis of -Diketones

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• 作者：Lezhen Li ; Peijie Cai ; Da Xu ; Qingxiang Guo ; Song Xue
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 12, 2007
• 年：2007
• 卷：72
• 期：21
• 页码：8131 - 8134
• 全文大小：107K
• 年卷期：v.72,no.21(October 12, 2007)
• ISSN：1520-6904

文摘

A new and efficient methodology has been developed forthe synthesis of -diketones from aromatic -bromo ketonesin the presence of Furukawa reagent under mild conditions.The present transformation is proposed to proceed via aReformatsky-type reaction of -bromo ketones, followed byC-C bond sigmatropic rearrangement of the aldolate intermediate to give -diketones in moderate to good isolatedyields, while aliphatic -bromomethyl ketones resulted inthe formation of 2,4-disubstituted furans or cis-1,2-disubstituted cyclopropanols in moderate yields. The scope of thisprocess was investigated, and a tentative mechanism wasproposed.