Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 17, Pages 7768-7774Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3015769
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Funding
- American Chemical Society Petroleum Research Fund [42856-GB1]
- National Science Foundation [CHE-0958425]
- Division Of Chemistry
- 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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