Silylamines in organic synthesis. Reactivity of N,N-bis(silyl)enamines toward electrophiles. A route to substituted 2-aza-1,3-butadienes and pyridines

Abstract

N,N-Bis(silyl) enamines exhibit very weak nucleophilic character when compared to carbon enamines or enol silyl ethers. They are stable to many electrophilic reagents under usual reaction conditions. In the presence of a nucleophilic catalyst, however, enamines appear quite reactive toward carbonyl compounds. Upon activation of the Si-N bond, aza dienes, enamidines, and pyridines are selectively obtained