Studies on the regioselectivity of Horner-Wadsworth-Emmons (HWE) reactions on 3,4-enuloses. Further evidence of phosphonate-phosphate rearrangements through five membered cyclic intermediates
The Horner-Wadsworth-Emmons (HWE) reaction was performed on methyl 3,6-di-0-benzoyl-2-deoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (1) with the potassium enolates of dimethyl [(methoxycarbonyl)methyl]phosphonate (2) or diethyl [(ethoxycarbonyl) methyl]phosphonate (3) under different conditions (meta...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
Marcel Dekker Inc.
1999
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 03926caa a22004457a 4500 | ||
|---|---|---|---|
| 001 | PAPER-2509 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203155.0 | ||
| 008 | 190411s1999 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0033241227 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JCACD | ||
| 100 | 1 | |a Moradei, O.M. | |
| 245 | 1 | 0 | |a Studies on the regioselectivity of Horner-Wadsworth-Emmons (HWE) reactions on 3,4-enuloses. Further evidence of phosphonate-phosphate rearrangements through five membered cyclic intermediates |
| 260 | |b Marcel Dekker Inc. |c 1999 | ||
| 270 | 1 | 0 | |m Moradei, O.M.; CIHIDECAR Depto. de Quim. Organ., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Moradei, O., Du Mortier, C., Fernández Cirelli, A., (1997) Tetrahedron, 53, p. 7397 | ||
| 504 | |a Deschamps, B., Seyden-Penne, J., (1977) Tetrahedron, 33, p. 413 | ||
| 504 | |a Buchanan, G.W., Bowen, J.H., (1977) Can. J. Chem., 55, p. 604 | ||
| 504 | |a Buchanan, G.W., Benezra, C., (1976) Can. J. Chem., 54, p. 231 | ||
| 504 | |a Strzalko, T., Corset, J., Froment, F., Pouet, M., Seyden-Penne, J., Simonnin, M., (1980) J. Org. Chem., 45, p. 1270 | ||
| 504 | |a Boschelli, D., Takemasa, T., Nishitani, Y., Masamune, S., (1985) Tetrahedron Lett., 26, p. 5239 | ||
| 504 | |a Moradei, O., Du Mortier, C., Fernández Cirelli, A., Thiem, J., (1999) J. Carbohydr. Chem., 18, p. 15 | ||
| 504 | |a Cossentini, M., Deschamps, B., Trong Anh, N., Seyden-Penne, J., (1977) Tetrahedron, 33, p. 409 | ||
| 520 | 3 | |a The Horner-Wadsworth-Emmons (HWE) reaction was performed on methyl 3,6-di-0-benzoyl-2-deoxy-α-D-glycero-hex-2-enopyranosid-4-ulose (1) with the potassium enolates of dimethyl [(methoxycarbonyl)methyl]phosphonate (2) or diethyl [(ethoxycarbonyl) methyl]phosphonate (3) under different conditions (metallic cation and solvent) in order to study regio- and stereochemical aspects of the reaction. In the presence of lithium ions, no reaction took place. When sodium enolates were employed, 1,2-addition was the main reaction in chelating solvents, whereas the 1,4-adduct is favoured in the less polar, non chelating toluene. Only 1,2-addition was observed with potassium enolates. Evidence of phosphonate-phosphate rearrangements through five membered cyclic intermediates is described. |l eng | |
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: We wish to thank Universidad de Buenos Aires and Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET) for financial support and UMYMFOR for the microanalyses. A. Fernandez Cirelli is a Research Member in CONICET. | ||
| 593 | |a CIHIDECAR Depto. de Quim. Organ., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a Du Mortier, C.M. | |
| 700 | 1 | |a Fernández Cirelli, A. | |
| 773 | 0 | |d Marcel Dekker Inc., 1999 |g v. 18 |h pp. 709-719 |k n. 6 |p J. Carbohydr. Chem. |x 07328303 |w (AR-BaUEN)CENRE-573 |t Journal of Carbohydrate Chemistry | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033241227&doi=10.1080%2f07328309908544032&partnerID=40&md5=3e13a81bb3a409d5ab4b5ded6800b981 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1080/07328309908544032 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_07328303_v18_n6_p709_Moradei |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07328303_v18_n6_p709_Moradei |y Registro en la Biblioteca Digital |
| 961 | |a paper_07328303_v18_n6_p709_Moradei |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 63462 | ||