Phosphine-Triggered Tandem Annulation between Morita鈥揃aylis鈥揌illman Carbonates and Dinucleophiles: Facile Syntheses of Oxazepanes, Thiazepanes, and Diazepanes

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• 作者：Rong Zhou ; Jianfang Wang ; Chong Duan ; Zhengjie He
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：December 21, 2012
• 年：2012
• 卷：14
• 期：24
• 页码：6134-6137
• 全文大小：238K
• 年卷期：v.14,no.24(December 21, 2012)
• ISSN：1523-7052

文摘

A new phosphine-triggered tandem [3 + 4] annulation reaction between Morita鈥揃aylis鈥揌illman carbonates and 1,4-diheteroatom dinucleophiles has been developed, which provides a facile synthetic method for saturated seven-membered 1,4-heterocycles such as 1,4-oxazepanes, 1,4-thiazepanes, and 1,4-diazepanes. Mechanistic investigation implies that this reaction takes place through a phosphine-catalyzed allylic alkylation followed by a general base-catalyzed intramolecular Michael cyclization.