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

SMN Sieburth, JJ Somers, HK O'Hare

Index: Sieburth, Scott McN.; Somers, Joseph J.; O'Hare, Heather K. Tetrahedron, 1996 , vol. 52, # 16 p. 5669 - 5682

Full Text: HTML

Citation Number: 15

Abstract

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. Metalation of tert-butyl carbamate derivatives ...