Indium(III) chloride-promoted intramolecular addition of allylstannanes to alkynes |
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| Authors: | Miura Katsukiyo Fujisawa Naoki Hosomi Akira |
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| Affiliation: | Department of Chemistry, 21st Century COE, Graduate School of Pure and Applied Sciences, University of Tsukuba, and CREST, Japan Science and Technology Corporation (JST), Tsukuba, Ibaraki 305-8571, Japan. miura@chem.tsukuba.ac.jp |
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| Abstract: | In the presence of an equimolar amount of InCl(3), 8-tributylstannyl-6-octen-1-ynes (allylstannanes bearing an alkynyl group) were efficiently cyclized to 2-allyl-1-methylenecyclopentanes. In contrast, catalytic use of InCl(3) gave 2-allyl-1-(tributylstannylmethylene)cyclopentanes mainly by intramolecular allylstannylation. These cyclizations could proceed via intramolecular addition of an allylindium intermediate. |
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