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The Intramolecular Allenolate Rauhut–Currier Reaction

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journal contribution
posted on 07.09.2012, 00:00 by James A. MacKay, Zachary C. Landis, Stephen E. Motika, Margaret H. Kench
An intramolecular Rauhut–Currier 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–C bond. Because of the highly electrophilic alkyne acceptor, this reaction yields products that cannot be easily accessed from the traditional Rauhut–Currier reaction.