Enantioselective Reduction of 1-Naphthamides by Electrochemical Reduction and Catalytic Asymmetric Hydrogenation in Tandem

Abstract

Chiral 1-tetrahydronaphthamides are the core structures of many bioactive molecules, yet their efficient asymmetric synthesis from a simple feedstock remains a challenge. Herein, we present a one-pot synthesis strategy that combines electrochemical reduction and ruthenium-catalyzed asymmetric hydrogenation to achieve the enantioselective reduction of 1-naphthalenamides to chiral 1-tetrahydronaphthamides. The protocol provides a practical platform for selectively constructing high-value chiral tetrahydronaphthenes from readily available naphthalene feedstock, thereby expanding the scope of asymmetric hydrogenation. The synthetic utility of this protocol is further demonstrated through the synthesis of bioactive molecules.