Tetrahedron

A stereoselective synthesis of silylated polyunsaturated halides from α, β-epoxysilanes

F Babudri, V Fiandanese, G Marchese, A Punzi

Index: Babudri, Francesco; Fiandanese, Vito; Marchese, Giuseppe; Punzi, Angela Tetrahedron, 2001 , vol. 57, # 3 p. 549 - 554

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Citation Number: 22

Abstract

A new synthetic approach to silylated polyunsaturated halides has been developed, starting from the readily available (1E, 3E)-1, 4-bis (trimethylsilyl)-1, 3-butadiene and (3E)-1, 4-bis (trimethylsilyl)-3-buten-1-yne. A simple epoxidation reaction, followed by regioselective α- opening of the epoxide ring by metal halides affords the corresponding halohydrins with a high degree of stereoselectivity. A subsequent β-elimination reaction from these ...