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DOI: 10.1055/s-2006-942538
Palladium-Catalyzed Cyclopentenone Formation by Carbonylative Cycloaddition of Allylic Tosylates and Alkynes
Publication History
Publication Date:
02 August 2006 (online)
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Abstract
Carbonylative cycloaddition of allyl tosylates and alkynes proceeded in the presence of palladium catalysts to afford a range of cyclopentenones. In the presence of methanol, five-component coupling reactions gave methyl cyclopentenyl acetates, whereas in the absence of methanol, (cyclopentenoylmethylidene)furanones were formed from six components. Allyl tosylate was found to be essential for these reactions, as allyl acetate and allyl bromide proved to be ineffective.
Key words
carbonylations - cycloadditions - palladium - alkynes - homogeneous catalysis
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References
The 2:1 ratio of palladium and PPh3 was also applied to the reactions in entries 5 and 6 because the yield of 7a was higher when using palladium and PPh3 in 2:1 ratio than in 1:1 ratio, although the 2:1 ratio is unusual.