An Efficient Method for Cyclopentene Annulation onto α, β-Unsaturated Ketones: W (CO) 5 (L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

N Iwasawa, T Miura, K Kiyota, H Kusama, K Lee…

Index: Miura, Tomoya; Iwasawa, Nobuharu Journal of the American Chemical Society, 2002 , vol. 124, # 4 p. 518 - 519

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Citation Number: 89

Abstract

A highly efficient method for the cyclopentene annulation onto α, β-unsaturated ketones is described. Indium-mediated 1, 4-propargylation onto α, β-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.