Enantioselective synthesis of ( S)-2-amino-3-phosphonopropionic acid, ( S)-AP-3, and ( R)-2-amino-4-phosphonobutanoic acid, ( R)-AP-4, via diastereoselective azidation of (4 R,5 R)- trans- N-[(diethoxyphosphoryl)propionyl]- and (4 R,5 R)- trans- N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

N-Acylation of readily available, enantiopure oxazolidinone (4 R,5 R)- 1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4 R,5 R)- 2 and (4 R,5 R)- 7, respectively, which are azidated with high diastereoselectivity by means of the r...

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Bibliographic Details
Published in:Tetrahedron 2006-08, Vol.62 (35), p.8404-8409
Main Authors: Reyes-Rangel, Gloria, Marañón, Virginia, Avila-Ortiz, C. Gabriela, Anaya de Parrodi, Cecilia, Quintero, Leticia, Juaristi, Eusebio
Format: Article
Language:English
Subjects:
Aminophosphonic acids
Chiral oxazolidinones
Diastereoselective electrophilic amination
Enantioselective synthesis
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Summary:N-Acylation of readily available, enantiopure oxazolidinone (4 R,5 R)- 1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4 R,5 R)- 2 and (4 R,5 R)- 7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4 R,5 R)- 2-Na and (4 R,5 R)- 7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4 R,5 R,2′ S)- 3 and (4 R,5 R,2′ R)- 8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids ( S)- 4 and ( R)- 9 gave the pharmacologically relevant aminophosphonic acids ( S)-AP-3 and ( R)-AP-4 in good yield. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.06.018