α-Alkyl-α-aminosilanes. 1. Metalation and alkylation between silicon and nitrogen

Article abstract of DOI:10.1016/0040-4020(96)00190-1

tert-Butyl carbamate derivatives of readily available aminomethyltrialkylsilanes have been studied for their ability to undergo metalation between nitrogen and silicon, followed by reaction with an electrophile. Metalation is rapid and reaction with a variety of electrophiles proceeds efficiently. When a benzyl group is attached to nitrogen, benzylic deprotonation competes with deprotonation next to silicon.