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

Weirong Wu
2014 Bulletin of the Korean Chemical Society (Print)  
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
more » ... sis 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 amidesin good to excellent yields. Scheme 1. Rao's L-proline and pyrrolidine-catalyzed transamidation of acetamide with benzylamine.
doi:10.5012/bkcs.2014.35.9.2673 fatcat:pnq6pforbnf5jkyvchuqaeu3o4