Silylcuprate Routes to Cyclohex-2-enylsilanes

Abstract

The efficacy of the dimethyl(phenyl)silylcuprate and (to a lesser extent) the methyl-diphenylsilylcuprate reagents in converting cyclohex-2-enyl chlorides into the corresponding allylsilanes has been investigated. The presence of copper(I) greatly suppresses formation of the coupled hydrocarbon, and promotes stereo- and regio-selective carbon-silicon bond formation, in a predominantly anti-S_N2′ manner. Spectroscopic characterization of the diastereomeric silanes is presented. Grignard routes to some of these silanes are described.