Theoretical Insight into the Mechanism of an Efficient L-Proline-catalyzed Transamidation of Acetamide with Benzylamine

摘要

The detailed mechanisms of the efficient L-proline and pyrrolidine catalyzed transamidation of acetamide with benzylamine have been investigated using density functional theory (DFT) calculations. Our calculated results show: (1) the mechanisms of two catalytic cycle reactions are similar. However, the rate-determining steps of their reactions are different for the whole catalytic process. One is the intramolecular nucleophilic addition reaction of 1-COM, the other is hydrolysis reaction of 2-C. (2) COOH group of L-proline is essential for efficient transamidation. The computational results are in good agreement withthe experiment finding and mechanism resported by Rao et al. for L-proline-catalyzed synthesis of amidesingood to excellent yields.