Tuning the Reactivity of O‐tert‐Butyldimethylsilylimidazolyl Aminals Towards Organolithium Reagents.

Abstract

Reactions of organo-metal compounds Reactions of organo-metal compounds O 0350Tuning the Reactivity of O-tert-Butyldimethylsilylimidazolyl Aminals Towards Organolithium Reagents. -The N,O-silylimidazoles aminals (II) react with organolithium reagents similarly to the parent aldehyde yielding secondary alcohols (IV). Since their mechanism of formation involves a silyl migration from the oxygen to the 2-position of the imidazole it is expected, that 2-substituted imidazoles are unreactive against organolithiums. Thus, the N,O-acetals (VII) are prepared and found to be stable at -78°C in the presence of organolithium reagents. -(GIMISIS*, T.; ARSENYAN, P.; GEORGANAKIS, D.; LEONDIADIS, L.; Synlett 2003, 10, 1451-1454; Lab. Org.