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The Intramolecular Allenolate Rauhut–Currier Reaction

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journal contribution
posted on 07.09.2012 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.