Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

Douglas Weibel, Vladimir Gevorgyan, Yoshinori Yamamoto

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Abstract

Several novel crownlike exomethylene paracyclophanes were efficiently synthesized via an intramolecular palladium-catalyzed benzannulation of conjugated bis-enynes. A method for the efficient synthesis of bis-enynes 8, bearing an oligo(oxyethylene) linkage, was developed by utilizing a two-step procedure from commercially available and inexpensive ethylene glycols. A remarkable complete reversal of reactivity of ambident dilithiated nucleophile 4 toward triflate 7 in the presence of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was found.

Original languageEnglish (US)
Pages (from-to)1217-1220
Number of pages4
JournalJournal of Organic Chemistry
Volume63
Issue number4
DOIs
StatePublished - Feb 20 1998

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ASJC Scopus subject areas

  • Organic Chemistry

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