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Updated: May 25, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Dual-function of alcohols in gold-mediated selective coupling of amines and alcohols
Bingjun Xu1, Robert J Madix, Cynthia M Friend
1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA.
Abstract:
Oxidative coupling of alcohols (methanol and ethanol) and dimethylamine on atomic-oxygen-activated Au(111) occurs entirely on the surface to form the corresponding amides when the alkoxy of the alcohol and the amide derived from the amine are co-adsorbed. For effective oxygen-assisted coupling the formation of the amide requires excess methanol. Mechanistic studies reveal that molecularly adsorbed methanol removes excess adsorbed atomic oxygen efficiently, precluding either secondary oxidation or oxidative dehydrogenation of dimethylamide to the imine. The adsorbed amide then can react with the aldehyde produced by β-hydride elimination from the alkoxy to form the hemiaminal, the reactive intermediate leading to coupling. The selectivity for formamide production can be increased to nearly 100 % in excess methanol.
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