: 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.
ASJC Scopus subject areas
- Organic Chemistry