Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans

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• 作者：Carla Alamillo-Ferrer ; Marianna Karabourniotis-Sotti ; Alan R. Kennedy ; Matthew Campbell ; Nicholas C. O. Tomkinson
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3102-3105
• 全文大小：372K
• 年卷期：0
• ISSN：1523-7052

文摘

Treatment of homoallylic alcohols or carboxylic acids with malonoyl peroxide 1 provides a stereoselective method for the preparation of tetrahydrofurans, γ-lactones, and isobenzofuranones in 44–82% yield and up to 27:1 trans selectivity. Application of this simple and effective heterocyclization in the synthesis of the antidepressant citalopram is also described.