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Synthese und Charakterisierung von β‐phosphoranalogen Asparaginsäure‐Derivaten: 2‐Amino‐3‐aryl‐3‐phosphorylpropionsäure‐Derivate
Author(s) -
Preußler Carola,
Schnepp Kathrin,
Kellner Kurt
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101200
Subject(s) - chemistry , hydrolysis , alkali metal , oxazolone , aryl , alkaline hydrolysis , amino acid , medicinal chemistry , organic chemistry , stereochemistry , biochemistry , alkyl
Synthesis and Characterization of β‐Phosphorus Analogues of Aspartic Acid Derivatives: 2‐Amino‐3‐aryl‐3‐phosphorylpropionic Acid Derivatives The 4‐benzylidene‐4,5‐dihydro‐5‐oxazolones 1 react with alkali dialkyl phosphites 2 to give the alkali salts of 4‐[(dialkoxyphosphoryl)methyl]‐5‐hydroxyoxazoles 3 . Silylation of 3 with ClSiMe 3 yields the 5‐siloxyoxazole derivatives 4 . Treatment of 4 with alcohols or water provides 3‐aryl‐2‐(benzoylamino)‐3‐(dialkoxyphosphoryl)propionic acid esters 6 and propionic acids 7 , respectively. The ratio of the diastereomeres of 6 (A, B) and 7 (A, B) depends on the reaction conditions. A remarkable different diasteroselectivity is observed in basic versus acidic media. The proposed reaction pathway is supported by characterization of the intermediate 4‐[(dialkoxyphosphoryl)methyl]‐4,5‐dihydro‐5‐oxazolone 8 . A complete hydrolysis of compounds 6 produces the 3‐phosphonoaspartic acid 9 .