An efficient method for cyclopentene annulation onto alpha,beta-unsaturated ketones: W(CO)(5)(L)-catalyzed 5-endo-dig cyclization of 6-siloxy-5-en-1-ynes |
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Authors: | Iwasawa Nobuharu Miura Tomoya Kiyota Koichi Kusama Hiroyuki Lee Kooyeon Lee Phil Ho |
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Institution: | Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Japan. niwasawa@chem.titech.ac.jp |
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Abstract: | reaction: see text] A highly efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto alpha,beta-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)(5)(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield. |
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