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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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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.

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Key Words

Amides


ID: J48-Y2006-4120