In our laboratories we have developed a highly enantioselective one pot procedure for the synthesis of �-substituted amides starting from the corresponding a,�-unsaturated esters. This new methodology is based on the previously developed copper-catalysed asymmetric CA of Grignard reagents to a,�-unsaturated1 esters and the subsequent direct formation of the corresponding amides by quenching the enolate with an amine without the need of extra reagents. This methodology is compatible with a range of a,�-unsaturated esters, Grignard reagents and amines, including primary and secondary amines bearing alkyl or aryl substituents. Importantly, this one pot two-step process occurs without racemisation. Furthermore, the robustness of the process is demonstrated by performing the reaction on a 1.0 g scale.2 1 F. L�pez, S. Harutyunyan, A. Meetsma, A. J. Minnaard, B. L. Feringa, Angew. Chem., Int. Ed., 2005  , 44, 2752, S. Wang, S. Ji, T. Loh, J. Am. Chem. Soc., 2007  ,129, 276, S. Wang, T. Lum, S. Ji and T. Loh, Adv. Synth. Catal., 2008  , 350, 673 S. Wang and T. Loh, Chem. Commun., 2010 , 46, 8694.2 A.K. Schoonen, M. �ngeles Fern�ndez-Ib��ez, M. Fa�an�s-Mastral, J.F. Teichert, B.L. Feringa, Org. Biomol. Chem., 2014  , 12, 36

Chiral amides via copper-catalyzed enantioselective conjugate addition

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.