Catalytic Palladium-Mediated Tetraene Carbocyclizations

James M. Takacs, Jingyang Zhu

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Abstract

: A new palladium-catalyzed carbocyclization of substrates containing two 1,3-diene moieties leads to the efficient, stereoselective preparation of functionalized cy-clopentanes and pyrrolidines. Treatment of tetraenes with 5 mol % of a palladium catalyst and 2–10 equiv of an H-X trapping reagent effects carbocyclization under mild reaction conditions (25–65 °C) in good-to-excellent yields (50-94%) and with good-to-excellent stereoselectivity (5 to > 20:l, trans:cis). of particular note is the exceptional versatility of this methodology; versatility arising from the fact that the tetraene substrate is regioselectively coupled to an H-X (X = C, N, O, S) trapping reagent during the course of the cyclization.

Original languageEnglish (US)
Pages (from-to)5193-5195
Number of pages3
JournalJournal of Organic Chemistry
Volume54
Issue number22
DOIs
StatePublished - Oct 1 1989

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ASJC Scopus subject areas

  • Organic Chemistry

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