Artículo
Orgueira, H.A.; Varela, O. "Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6" (1997) Tetrahedron Asymmetry. 8(9):1383-1389
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Abstract:
L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13.
Registro:
| Documento: | Artículo |
| Título: | Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6 |
| Autor: | Orgueira, H.A.; Varela, O. |
| Filiación: | CIHIDECAR (CONICET) - Depto. Q., Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina |
| Palabras clave: | nylon; polymer; article; chirality; drug synthesis; in vitro study; nuclear magnetic resonance spectroscopy; priority journal; reaction analysis; stereochemistry |
| Año: | 1997 |
| Volumen: | 8 |
| Número: | 9 |
| Página de inicio: | 1383 |
| Página de fin: | 1389 |
| DOI: | http://dx.doi.org/10.1016/S0957-4166(97)00121-3 |
| Título revista: | Tetrahedron Asymmetry |
| Título revista abreviado: | TETRAHEDRON ASYMMETRY |
| ISSN: | 09574166 |
| CODEN: | TASYE |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v8_n9_p1383_Orgueira |
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Citas:
---------- APA ----------
Orgueira, H.A. & Varela, O. (1997) . Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6. Tetrahedron Asymmetry, 8(9), 1383-1389.http://dx.doi.org/10.1016/S0957-4166(97)00121-3
---------- CHICAGO ----------
Orgueira, H.A., Varela, O. "Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6" . Tetrahedron Asymmetry 8, no. 9 (1997) : 1383-1389.http://dx.doi.org/10.1016/S0957-4166(97)00121-3
---------- MLA ----------
Orgueira, H.A., Varela, O. "Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6" . Tetrahedron Asymmetry, vol. 8, no. 9, 1997, pp. 1383-1389.http://dx.doi.org/10.1016/S0957-4166(97)00121-3
---------- VANCOUVER ----------
Orgueira, H.A., Varela, O. Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6. TETRAHEDRON ASYMMETRY. 1997;8(9):1383-1389.http://dx.doi.org/10.1016/S0957-4166(97)00121-3
