title: The intramolecular allenolate Rauhut-Currier reaction.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Elizabethtown College, 1 Alpha Drive, Elizabethtown, Pennsylvania 17022, USA. mackayj@etown.edu
authors.forename: James A
authors.initials: JA
authors.lastname: MacKay
authors.forename: Zachary C
authors.initials: ZC
authors.lastname: Landis
authors.forename: Stephen E
authors.initials: SE
authors.lastname: Motika
authors.forename: Margaret H
authors.initials: MH
authors.lastname: Kench
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D009570:Nitriles; D010720:Phosphines