N-(Ethoxycarbonyl)-beta-amino-alpha-methylene phosphonic esters give N-(ethoxycarbonyl)-beta-amino-alpha-hydroxy phosphonic esters by ozonization and subsequent reduction with a large excess of NaBH4. If there is a small excess of NaBH4 or if the intermediate is treated with methanolic NaOH-CH2Cl2 an anomalous ozonolysis occurs, affording N-(ethoxycarbonyl)-alpha-amino methyl carboxylic esters due to the cleavage of both the C=C double bond and the adjacent C-P single bond

Francavilla, M., Gasperi, T., LORETO M., A., TARDELLA P., A., Bassetti, M. (2002). Ozonization and reduction of alpha-methylene N-(ethoxycarbonil)-beta-amino phosphonic esters. TETRAHEDRON LETTERS, 43, 7913-7916 [10.1016/S0040-4039(02)01906-8].

Ozonization and reduction of alpha-methylene N-(ethoxycarbonil)-beta-amino phosphonic esters

GASPERI, TECLA;
2002-01-01

Abstract

N-(Ethoxycarbonyl)-beta-amino-alpha-methylene phosphonic esters give N-(ethoxycarbonyl)-beta-amino-alpha-hydroxy phosphonic esters by ozonization and subsequent reduction with a large excess of NaBH4. If there is a small excess of NaBH4 or if the intermediate is treated with methanolic NaOH-CH2Cl2 an anomalous ozonolysis occurs, affording N-(ethoxycarbonyl)-alpha-amino methyl carboxylic esters due to the cleavage of both the C=C double bond and the adjacent C-P single bond
Francavilla, M., Gasperi, T., LORETO M., A., TARDELLA P., A., Bassetti, M. (2002). Ozonization and reduction of alpha-methylene N-(ethoxycarbonil)-beta-amino phosphonic esters. TETRAHEDRON LETTERS, 43, 7913-7916 [10.1016/S0040-4039(02)01906-8].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11590/132589
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