Enzyme-Like Chemoselective Acylation of Alcohols in the Presence of Amines Catalyzed by a Tetranuclear Zinc Cluster

摘要

Esters and amides are ubiquitous functional groups in natural and synthetic organic compounds, thus esterification and amidation are among the most fundamental and important reactions in organic synthesis. They are commonly synthesized by acylation of the corresponding alcohol and amine, respectively, with a carboxylic acid, an acid chloride, or an acid anhydride. As the nucleophilicity of the amino group is much greater than that of the hydroxyl group, the amine can be selectively acylated to give the corresponding amide, even in the presence of excess alcohols and/or water. This chemoselectivity has been well utilized for several highly efficient amidation reactions such as the Schotten-Baumann reactions (Scheme 1, path a, 1 → 2).