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Efficient synthesis of functionalized furans via ruthenium-catalyzed cyclization of epoxyalkyne derivatives
Ching-Yu Lo1, Hongyun Guo, Jian-Jou Lian
1Department of Chemistry, National Tsing-Hua University, Hsinchu, 30043 Taiwan, ROC.
The Journal of Organic Chemistry
|May 25, 2002
Abstract:
Ruthenium catalyst TpRuPPh(3)(CH(3)CN)(2)Cl is found to effect the cyclization of epoxyalkynes to furans in the presence of Et(3)N. The reactions worked well for various epoxyalkynes with suitable oxygen and nitrogen functionalities with low loading of catalyst. It failed with disubstituted epoxyalkynes. The mechanism was elucidated by a deuterium labeling experiment that suggested that the mechanism involved a ruthenium-vinylidenium intermediate.