A New and Efficient Synthesis of α-Amino Cycloalkyl-Phosphonic Acids via Electrophilic Azidation of Cycloalkylphosphonates |
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| Authors: | Catherine Guéguen Elie About-Jaude Noël Collignon Philippe Savignac |
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| Institution: | 1. Laboratoire d'Hétérochimie Organique , INSA-IRCOF , BP 08, 76131, Mont-Saint-Aignan, Cedex, FRANCE;2. Hétéroéléments et Coordination , URA CNRS , 1499, DCPH, Ecole Polytechnique, 91128, Palaiseau, Cedex, FRANCE |
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| 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). |
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