The <i>Si</i>-2,4,6-Trimethoxyphenyl Moiety as a Novel Protecting Group in Organosilicon Chemistry: Alternative Synthesis of <i>r</i><i>ac</i>-Sila-venlafaxine

Abstract

The Si-2,4,6-trimethoxyphenyl (Si-2,4,6-TMOP) moiety is claimed to be an effective protecting group for synthetic organosilicon chemistry. To demonstrate its high synthetic potential, the Si-2,4,6-TMOP protecting group has been used for a novel multistep synthesis of rac-sila-venlafaxine (a sila-analogue of the serotonin/noradrenaline reuptake inhibitor rac-venlafaxine), starting from 1,1-dichloro-1-silacyclohexane. In addition, the Si-2,4,6-TMOP moiety has been used as a protecting group in silacyclobutane chemistry.