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 (free Supporting Information)
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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.
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