Diversification of Unprotected Alicyclic Amines by C−H Bond Functionalization: Decarboxylative Alkylation of Transient Imines

Abstract

AbstractDespite extensive efforts by many practitioners in the field, methods for the direct α‐C−H bond functionalization of unprotected alicyclic amines remain rare. A new advance in this area utilizes N‐lithiated alicyclic amines. These readily accessible intermediates are converted to transient imines through the action of a simple ketone oxidant, followed by alkylation with a β‐ketoacid under mild conditions to provide valuable β‐amino ketones with unprecedented ease. Regioselective α′‐alkylation is achieved for substrates with existing α‐substituents. The method is further applicable to the convenient one‐pot synthesis of polycyclic dihydroquinolones through the incorporation of a SNAr step.