jo3015769_si_001.pdf (3.08 MB)
The Intramolecular Allenolate Rauhut–Currier Reaction
journal contribution
posted on 2012-09-07, 00:00 authored by James A. MacKay, Zachary C. Landis, Stephen E. Motika, Margaret
H. KenchAn 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.