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Abstract:

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.

Registro:

Documento: Artículo
Título: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
Autor:Moradei, O.M.; Du Mortier, C.M.; Fernández Cirelli, A.
Filiación:CIHIDECAR Depto. de Quim. Organ., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Año:1999
Volumen:18
Número:6
Página de inicio:709
Página de fin:719
DOI: http://dx.doi.org/10.1080/07328309908544032
Título revista:Journal of Carbohydrate Chemistry
Título revista abreviado:J. Carbohydr. Chem.
ISSN:07328303
CODEN:JCACD
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07328303_v18_n6_p709_Moradei

Referencias:

  • Moradei, O., Du Mortier, C., Fernández Cirelli, A., (1997) Tetrahedron, 53, p. 7397
  • Deschamps, B., Seyden-Penne, J., (1977) Tetrahedron, 33, p. 413
  • Buchanan, G.W., Bowen, J.H., (1977) Can. J. Chem., 55, p. 604
  • Buchanan, G.W., Benezra, C., (1976) Can. J. Chem., 54, p. 231
  • Strzalko, T., Corset, J., Froment, F., Pouet, M., Seyden-Penne, J., Simonnin, M., (1980) J. Org. Chem., 45, p. 1270
  • Boschelli, D., Takemasa, T., Nishitani, Y., Masamune, S., (1985) Tetrahedron Lett., 26, p. 5239
  • Moradei, O., Du Mortier, C., Fernández Cirelli, A., Thiem, J., (1999) J. Carbohydr. Chem., 18, p. 15
  • Cossentini, M., Deschamps, B., Trong Anh, N., Seyden-Penne, J., (1977) Tetrahedron, 33, p. 409

Citas:

---------- APA ----------
Moradei, O.M., Du Mortier, C.M. & Fernández Cirelli, A. (1999) . 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. Journal of Carbohydrate Chemistry, 18(6), 709-719.
http://dx.doi.org/10.1080/07328309908544032
---------- CHICAGO ----------
Moradei, O.M., Du Mortier, C.M., Fernández Cirelli, 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" . Journal of Carbohydrate Chemistry 18, no. 6 (1999) : 709-719.
http://dx.doi.org/10.1080/07328309908544032
---------- MLA ----------
Moradei, O.M., Du Mortier, C.M., Fernández Cirelli, 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" . Journal of Carbohydrate Chemistry, vol. 18, no. 6, 1999, pp. 709-719.
http://dx.doi.org/10.1080/07328309908544032
---------- VANCOUVER ----------
Moradei, O.M., Du Mortier, C.M., Fernández Cirelli, 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. J. Carbohydr. Chem. 1999;18(6):709-719.
http://dx.doi.org/10.1080/07328309908544032