The Intramolecular Allenolate Rauhut鈥揅urrier Reaction

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• 作者：James A. MacKay ; Zachary C. Landis ; Stephen E. Motika ; Margaret H. Kench
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：September 7, 2012
• 年：2012
• 卷：77
• 期：17
• 页码：7768-7774
• 全文大小：339K
• 年卷期：v.77,no.17(September 7, 2012)
• ISSN：1520-6904

文摘

An intramolecular Rauhut鈥揅urrier reaction utilizing alkynoates as the initial conjugate acceptor affords densely functionalized 5- and 6-membered rings from ynoate-enoate, ynoate-enenitrile, and alkynyl sulfone-enenitrile substrates. Trialkylphosphines catalyze the reaction, and TMSCN serves as a pronucelophile to effect turnover of the catalyst and the formation of a second C鈥揅 bond. Because of the highly electrophilic alkyne acceptor, this reaction yields products that cannot be easily accessed from the traditional Rauhut鈥揅urrier reaction.