Enantioselective catalytic oxidation of 1-phenylethanol chiral nitroxyl radical-terminated self-assembled monolayer modified electrode

Thiol derivatized (6S,7R,10R)-4-amino-2,2,7-trimethyl-10-isopropyl-1-azaspi ro[5.5]undecane-1-yloxyl was synthesized to modify the surface of a gold el ectrode with its self-assembled monolayer. This modified electrode showed s ymmetrical reversible redox wave at +0.62 V vs. Ag/AgCl, which originates f rom the electron transfer between the self-assembled monolayer and electrod e. The modified electrode exhibited an enantioselective catalytic oxidation for chiral secondary alcohols; (S)-(-)-1-phenylethanol was oxidized into t he ketone more efficiently than (R)-(+)-1-phenylethanol.