An effcient protocol for accessing β-Amino dicarbonyl compounds through aza-Michael reaction

Abstract

β-Amino dicarbonyl compounds comprise a class of useful ligands on the coordination chemistry. In view of their importance, an effcient and facile method for the synthesis of β-amino dicarbonyl compounds has been developed, exploring the aza-Michael addition reactions in an aqueous medium. It was possible to achieve good to excellent yields, along with regioselectivity, the substituted diethyl 2-(phenylmethyl)malonates that were easily isolated without any chromatographic purifcation. The correct confguration of two of these β-amino dicarbonyl compounds were confrmed by X-ray crystallography. A complementary mechanism of this aza-Michael protocol is proposed to explain the results obtained. © 2010 Sociedade Brasileira de Química.