Redox-Neutral [alpha],[beta]-Difunctionalization of Cyclic Amines

In contrast to the continuously growing number of methods that allow for the efficient [alpha]-functionalization of amines, few strategies exist that enable the direct functionalization of amines in the [beta]-position. A general redox-neutral strategy is outlined for amine [beta]-functionalization and [alpha],[beta]-difunctionalization that utilizes enamines generated insitu. This concept is demonstrated in the context of preparing polycyclic N,O-acetals from simple 1-(aminomethyl)-[beta]-naphthols and 2-(aminomethyl)-phenols. [PUBLICATION ABSTRACT]