W (CO) 5 (L)-Catalyzed Endo-Selective Cyclization of Allenyl Silyl Enol Ethers: An Efficient Method for the Cyclopentene Annulation onto α, β-Unsaturated Ketones

T Miura, K Kiyota, H Kusama, K Lee, H Kim, S Kim…

Index: Miura, Tomoya; Kiyota, Koichi; Kusama, Hiroyuki; Lee, Kooyeon; Kim, Hyunseok; Kim, Sunggak; Lee, Phil Ho; Iwasawa, Nobuharu Organic Letters, 2003 , vol. 5, # 10 p. 1725 - 1728

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Citation Number: 41

Abstract

Indium-mediated allenylation of α, β-unsaturated ketones in the presence of tert- butyldimethylsilyl triflate and dimethyl sulfide gives 6-siloxy-1, 2, 5-trienes, which undergo W (CO) 5 (L)-catalyzed 5-endo cyclization to give the corresponding cyclopentene derivatives in good yield. Furthermore, this novel W (CO) 5 (L)-catalyzed cyclization of allenyl silyl enol ethers proceeds in a 6-endo manner when 5-siloxy-1, 2, 5-trienes are employed as a ...