Selective 鈥淥ne-Pot鈥?Synthesis of Functionalized Cyclopentenones

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• 作者：Teresa Varea ; Ana Alcalde ; Carolina L贸pez de Dicastillo ; Carmen Ram铆rez de Arellano ; Fernando P. Coss铆o ; Gregorio Asensio
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：July 20, 2012
• 年：2012
• 卷：77
• 期：14
• 页码：6327-6331
• 全文大小：321K
• 年卷期：v.77,no.14(July 20, 2012)
• ISSN：1520-6904

文摘

Double addition (1,2鈥?,4) of vinyl magnesium bromide to squaric acid derivatives allows the preparation of polyoxygenated cyclopentenones (8) in a 鈥渙ne-pot鈥?procedure. The reaction occurs through the intermediate formation of octatetraenes (6). Protonation of this latter intermediate at 鈭?8 掳C with TFE occurs selectively at the vinyl CH₂ closer to the metallic centers. DFT studies of the cyclization step justify the observed diastereoselectivity.