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Redox-Neutral α,β-Difunctionalization of Cyclic Amines


  • Financial support from the NIH-NIGMS (R01GM101389-01) is gratefully acknowledged. We thank Dr. Tom Emge for crystallographic analysis.


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

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