4.7 Article

The Intramolecular Allenolate Rauhut-Currier Reaction

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 17, Pages 7768-7774

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo3015769

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Funding

  1. American Chemical Society Petroleum Research Fund [42856-GB1]
  2. National Science Foundation [CHE-0958425]
  3. Division Of Chemistry
  4. Direct For Mathematical & Physical Scien [0958425] Funding Source: National Science Foundation

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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.

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