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].
Titolo: | Ozonization and reduction of alpha-methylene N-(ethoxycarbonil)-beta-amino phosphonic esters | |
Autori: | ||
Data di pubblicazione: | 2002 | |
Rivista: | ||
Citazione: | 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]. | |
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 | |
Handle: | http://hdl.handle.net/11590/132589 | |
Appare nelle tipologie: | 1.1 Articolo in rivista |