Efficient Transamidation of Primary Carboxamides by in Situ Activation with N,N-Dialkylformamide Dimethyl Acetals
Thomas A. Dineen, Matthew A. Zajac and Andrew G. Myers*
*Contribution from the Department of Chemistry and Chemical Biology, Harvard
University, Cambridge, Massachusetts 02138, Email: myerschemistry.harvard.edu
T. A. Dineen, M. A. Zajac, A. G. Myers, J. Am. Chem. Soc., 2006, 128, 16406-16409.
DOI: 10.1021/ja066728i
see article for more reactions
Abstract
The reaction of N,N-dialkylformamide dimethyl acetal with primary amides produces N'-acyl-N,N-dialkylformamidines as intermediates. In the presence of certain Lewis acid additives efficient acyl transfer occurs, providing new and useful methods for amide exchange such as transamidation.
see article for more examples
Key Words
Amides, Transamidation
ID: J48-Y2006-4120