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The Intramolecular Allenolate Rauhut–Currier Reaction

By James A. MacKay (1809823), Zachary C. Landis (2047297), Stephen E. Motika (2047291) and Margaret H. Kench (2047294)


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

Topics: Biophysics, Biochemistry, Microbiology, Genetics, Molecular Biology, Pharmacology, Biotechnology, Evolutionary Biology, Sociology, Developmental Biology, Plant Biology, Virology, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, effect turnover, reaction yields products, Trialkylphosphines catalyze, Rauhut, TMSCN, electrophilic alkyne acceptor, conjugate acceptor
Year: 2012
DOI identifier: 10.1021/jo3015769.s001
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Provided by: FigShare
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