American Chemical Society
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A New Route to Cyclopentenones via Ruthenium-Catalyzed Carbonylative Cyclization of Allylic Carbonates with Alkenes

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journal contribution
posted on 2000-03-09, 00:00 authored by Yasuhiro Morisaki, Teruyuki Kondo, Take-aki Mitsudo
[RuCl2(CO)3]2/Et3N and (η3-C3H5)RuBr(CO)3/Et3N are highly effective catalyst systems for carbonylative cyclization of allylic carbonates with alkenes to give the corresponding cyclopentenones in high yields. For example, treatment of allyl methyl carbonate (1a) with 2-norbornene (2a) in the presence of a catalytic amount of [RuCl2(CO)3]2 (2.5 mol %) and Et3N (10 mol %) at 120 °C for 5 h under 3 atm of carbon monoxide gave the corresponding cyclopentenone, exo-4-methyltricyclo[,6]dec-4-en-3-one (3a), in 80% yield with high stereoselectivity (exo 100%).