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Synfacts 2007(1): 0087-0087  
DOI: 10.1055/s-2006-955701
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

AlMe3-DABCO-Promoted Synthesis of Amides

Contributor(s): Paul Knochel, Andrei Gavryushin
A. Novak, L. D. Humphreys, M. D. Walker, S. Woodward*
The University of Nottingham and Glaxosmithkline, Stevenage, UK
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Mild and direct formation of amides from amines and esters is of great interest as a synthetic method. Organoaluminum reagents are often used as catalysts for this process, but their pyrophoric nature is a significant drawback. The use of the safe and air-stable DABAL-Me3 (AlMe3-DABCO) complex represents an excellent alternative to the previously reported reagents. A broad range of primary amines can be used for this reaction. α-Hydroxy and β-keto esters are also good substrates and in the case of ethyl lactate, complete retention of chirality was observed.