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http://dx.doi.org/10.5012/bkcs.2014.35.9.2673

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

Wu, Weirong (Key Laboratory of Inorganic Chemistry in Universities of Shandong, Department of Chemistry and Chemical Engineering, Jining University)
Publication Information
Bulletin of the Korean Chemical Society / v.35, no.9, 2014 , pp. 2673-2678 More about this Journal
Abstract
The detailed mechanisms of the efficient $\small{L}$-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 $\small{L}$-proline is essential for efficient transamidation. The computational results are in good agreement with the experiment finding and mechanism resported by Rao et al. for $\small{L}$-proline-catalyzed synthesis of amidesin good to excellent yields.
Keywords
Transamidation; $\small{L}$-Proline-catalydst; Pyrrolidine-catalydst; Acetamide; Benzylamine;
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