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Communication | Special issue | Vol 67, No. 1, 2006, pp.101-105
Published online, 23rd August, 2005
DOI: 10.3987/COM-05-S(T)27
Rhodium-catalyzed Cycloisomerization of Allyl Propargyl Ethers: An Efficient Synthesis of 3,4-Disubstituted Furans

Hiroshi Kawai, Shuichi Oi,* and Yoshio Inoue*

*Graduate School of Engineering, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Cycloisomerization of allyl propargyl ethers was found to be catalyzed by a cationic rhodium complex to give 3,4-disubstituted furans in one step. Addition of carboxylic acids to the reaction improved the yield of the products. Generation of a rhodium hydride species from a rhodium complex with the carboxylic acids followed by hydrorhodation of the substrate with the rhodium hydride species would be involved in the reaction pathway.