The Intramolecular Allenolate
Rauhut–Currier Reaction

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

doi:10.1021/jo3015769.s001

The Intramolecular Allenolate Rauhut–Currier Reaction

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

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

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

OAI identifier: oai:figshare.com:article/2489428

Provided by: FigShare

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The Intramolecular Allenolate Rauhut–Currier Reaction

Abstract

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