The intramolecular allenolate rauhut-currier reaction

James A. MacKay, Elizabethtown College
Zachary C. Landis, Elizabethtown College
Stephen E. Motika, Elizabethtown College
Margaret H. Kench, Elizabethtown College


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. © 2012 American Chemical Society.