Catalytic Palladium-Mediated Tetraene Carbocyclizations

James M Takacs, Jingyang Zhu

Research output: Contribution to journalArticle

30 Citations (Scopus)

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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Palladium
Pyrrolidines
Stereoselectivity
Cyclization
Substrates
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Catalytic Palladium-Mediated Tetraene Carbocyclizations. / Takacs, James M; Zhu, Jingyang.

In: Journal of Organic Chemistry, Vol. 54, No. 22, 01.10.1989, p. 5193-5195.

Research output: Contribution to journalArticle

Takacs, James M ; Zhu, Jingyang. / Catalytic Palladium-Mediated Tetraene Carbocyclizations. In: Journal of Organic Chemistry. 1989 ; Vol. 54, No. 22. pp. 5193-5195.
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AB - : 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.

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