Palladium-Catalyzed Cyclopentenone Formation by Carbonylative Cycloaddition of Allylic Tosylates and Alkynes

Naofumi Tsukada; Shuichi Sugawara; Tomohiro Okuzawa; Yoshio Inoue

doi:10.1055/s-2006-942538

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Palladium-Catalyzed Cyclopentenone Formation by Carbonylative Cycloaddition of Allylic Tosylates and Alkynes

Naofumi Tsukada*, Shuichi Sugawara, Tomohiro Okuzawa, Yoshio Inoue
Graduate School of Engineering, Tohoku University, Sendai 980-8579, Japan
Fax: +81(22)7955876; e-Mail: tsukada@aporg.che.tohoku.ac.jp;

Abstract

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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

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