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 cl-opening of the epoxide ring by metal halides affords the corresponding halohydrins with a high degree of stereoselectivity. A subsequent p-elimination reaction from these compounds leads to (Z,E)-dienyl halides and to (Z)-enyne halides. (C) 2001 Elsevier Science Ltd. All rights reserved.

A stereoselective synthesis of silylated polyunsaturated halides from alpha,beta-epoxysilanes

BABUDRI, Francesco;PUNZI, Angela
2001-01-01

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 cl-opening of the epoxide ring by metal halides affords the corresponding halohydrins with a high degree of stereoselectivity. A subsequent p-elimination reaction from these compounds leads to (Z,E)-dienyl halides and to (Z)-enyne halides. (C) 2001 Elsevier Science Ltd. All rights reserved.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11586/131313
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