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

Douglas Weibel, Vladimir Gevorgyan, Yoshinori Yamamoto

Research output: Contribution to journalArticle

39 Citations (Scopus)

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
Externally publishedYes

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Ethylene Glycols
Bearings (structural)
Pyrimidinones
Nucleophiles
Polyethers
Palladium

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of Polyether Exomethylene Paracyclophanes via an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol. / Weibel, Douglas; Gevorgyan, Vladimir; Yamamoto, Yoshinori.

In: Journal of Organic Chemistry, Vol. 63, No. 4, 20.02.1998, p. 1217-1220.

Research output: Contribution to journalArticle

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