Lewis acid-mediated intramolecular addition of silyl enol ethers to internal unactivated alkynes

K Imamura, E Yoshikawa, V Gevorgyan…

Index: Imamura, Ken-Ichiro; Yoshikawa, Eiji; Gevorgyan, Vladimir; Sudo, Tomoko; Asao, Naoki; Yamamoto, Yoshinori Canadian Journal of Chemistry, 2001 , vol. 79, # 11 p. 1624 - 1631

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Citation Number: 14

Abstract

The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, gave mono-and bicyclic β, γ-unsaturated ketones in good to excellent yields. On the other hand, the silyloxy-substituted cyclic vinylsilanes were obtained in moderate to high yields when the reactions were catalyzed by B (C6F5) 3 in the presence of triethylsilane. All the ...