Efficient synthesis of racemic β-aminophosphonates via aza-Michael reaction in water

EV Matveeva, PV Petrovskii, IL Odinets

Index: Matveeva, Ekaterina V.; Petrovskii, Pavel V.; Odinets, Irina L. Tetrahedron Letters, 2008 , vol. 49, # 42 p. 6129 - 6133

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Citation Number: 28

Abstract

Water as a solvent significantly accelerates the addition of various amines to diethyl vinylphosphonate to yield β-aminophosphonates without any catalyst compared to known procedures for such aza-Michael reactions. The products are obtained in quantitative yields and high purity over short reaction times. Using a reactant ratio (vinylphosphonate/amine) of 2: 1 resulted in double phosphorylation of primary amines.