The Si-2,4,6-trimethoxyphenyl moiety as a novel protecting group in organosilicon chemistry:: Alternative synthesis of rac-sila-venlafaxine

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.