Ethenylation of silyl enol ether with silylethyne

M Yamaguchi, T Tsukagoshi…

Index: Yamaguchi, Masahiko; Tsukagoshi, Toru; Arisawa, Mieko Journal of the American Chemical Society, 1999 , vol. 121, # 16 p. 4074 - 4075

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Citation Number: 65

Abstract

Alkylation of enolate is one of the most fundamental carboncarbon bond formations in organic synthesis, and it is used to attach an sp3-carbon atom to the carbonyl R-carbon atom. Such enolate reaction at an sp2-carbon atom, however, has been problematic, due to the inertness of vinyl halides or acetylenes toward metal enolates. Enolate usually does not undergo SN1 and SN2 reactions with vinylic halides, and does not add to acetylenes. ...