Spirocyclopropanation Reaction of para-Quinone Methides with Sulfonium Salts: The Synthesis of Spirocyclopropanyl para-Dienones

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• 作者：Xiang-Zhi Zhang ; Ji-Yuan Du ; Yu-Hua Deng ; Wen-Dao Chu ; Xu Yan ; Ke-Yin Yu ; Chun-An Fan
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：March 18, 2016
• 年：2016
• 卷：81
• 期：6
• 页码：2598-2606
• 全文大小：594K
• ISSN：1520-6904

文摘

A novel DBU-mediated stereoselective spirocyclopropanation of para-quinone methides with sulfonium salts has been developed on the basis of the mode involving a 1,6-conjugate addition/intramolecular dearomatizing cyclization cascade. This reaction provides a mild and effective method for the assembly of synthetically and structurally interesting spirocyclopropanyl para-dienones. The feasibility for the enantioselective access to such functionalized para-dienones has also been explored by using the axially chiral sulfonium salt. Importantly, the regioselective ring openings of the related spirocyclopropanyl para-dienones have been achieved divergently.