A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic Acids via Electrophilic Azidation of Cycloalkylphosphonates

Abstract

α-Amino cyclobutyl-, cyclopentyl-and cyclohexylphosphonic acids (13) were efficiently prepared from the related unsubstituted cycloalkylphosphonates (5), in three steps including electrophilic azidation of the corresponding lithiated carbanions, catalytic hydrogenation of the intermediate α-azido cycloalkyl-phosphonates (10) and acidic hydrolysis of the resulting α-amino cycloalkyl-phosphonates (12).