Formal [3 + 2] Reaction of α,α-Diaryl Allylic Alcohols with sec-Alcohols: Proceeding with Sequential Radical Addition/Migration toward 2,3-Dihydrofurans Bearing Quaternary Carbon Centers

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• 作者：Weiming Hu ; Song Sun ; Jiang Cheng
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：81
• 期：10
• 页码：4399-4405
• 全文大小：452K
• 年卷期：0
• ISSN：1520-6904

文摘

An unprecedented TBHP-promoted formal [3 + 2] annulation of sec-alcohols with α,α-diaryl allylic alcohols has been developed, leading to 2,3-dihydrofurans in moderate to excellent yields with good functional group tolerance. This procedure involves sequential radical addition, 1,2-aryl migration, and a dehydration process, where the migration of aryl with lower electron density is favored. Notably, cyclic reactions with sec-alcohols also ran smoothly, providing a novel method to access oxaspiro compounds.