Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones

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The influence of such Lewis acids as Et2O·BF3, ZnCl2, SnCl4 and TiCl4 on the stereochemical course of the Diels-Alder cycloadditions of sugar-derived (2S)-alkoxydihydropyranones was studied. The first two catalysts promoted the addition of dienes to give (3S,4aR,8aS)-3-alkoxy-4a,5,8,8a-tetrahydro-2-...

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Autor principal: Iriarte Capaccio, C.A
Otros Autores: Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: Elsevier Ltd 2003
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Iriarte Capaccio, C.A. 
245 1 0 |a Influence of Lewis acids on the facial selectivity in cycloadditions of sugar-derived dihydropyranones 
260 |b Elsevier Ltd  |c 2003 
270 1 0 |m Varela, O.; CIHIDECAR-CONICET, Depto. de Quím. Orgán., Pabellón II, 1428 Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Oppolzer, W., (1984) Angew. Chem., Int. Ed. Engl., 23, pp. 876-889 
504 |a Oppolzer, W., (1991) Comprehensive Organic Synthesis: Selectivity, Strategy & Efficiency in Modern Organic Chemistry, 5, pp. 315-399. , B.M. Trost, I. Fleming, Paquette L.A. Oxford: Pergamon 
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504 |a Corey, E.J., Guzman-Perez, A., (1998) Angew. Chem., Int. Ed. Engl., 37, pp. 388-401 
504 |a Corey, E.J., (2002) Angew. Chem., Int. Ed. Engl., 41, pp. 1650-1667 
504 |a Nicolaou, K.C., Snyder, S.A., Montagnon, T., Vassilikogiannakis, G., (2002) Angew. Chem., Int. Ed. Engl., 41, pp. 1668-1698 
504 |a Gawley, R.E., Aubé, J., (1996) Principles of Asymmetric Synthesis, Tetrahedron Organic Chemistry Series, 14, pp. 263-291. , J.E. Baldwin, Magnus P.D. Oxford: Pergamon 
504 |a Houk, K.N., González, J., Li, Y., (1995) Acc. Chem. Res., 28, pp. 81-90 
504 |a Beno, B.R., Houk, K.N., Singleton, D.A., (1996) J. Am. Chem. Soc., 118, pp. 9984-9985 
504 |a Sauer, J., Sustmann, R., (1980) Angew. Chem., Int. Ed. Engl., 19, pp. 779-807 
504 |a Birney, D.M., Houk, K.N., (1990) J. Am. Chem. Soc., 112, pp. 4127-4133 
504 |a Reetz, M.T., (1984) Angew. Chem., Int. Ed. Engl., 23, pp. 556-569 
504 |a Reetz, M.T., Hüllmann, M., Massa, W., Berger, S., Rademacher, P., Heymanns, P., (1986) J. Am. Chem. Soc., 108, pp. 2405-2408 
504 |a Heathcock, C.H., Flippin, L.A., (1983) J. Am. Chem. Soc., 105, pp. 1667-1668 
504 |a Danishefsky, S.J., Pearson, W.H., Harvey, D.F., (1984) J. Am. Chem. Soc., 106, pp. 2456-2458 
504 |a Poll, T., Metter, J.O., Helmchen, G., (1985) Angew. Chem., Int. Ed. Engl., 24, pp. 112-114 
504 |a Evans, D.A., Chapman, K.T., Bisaha, J., (1988) J. Am. Chem. Soc., 110, pp. 1238-1256 
504 |a Iriarte Capaccio, C.A., Varela, O., (2001) J. Org. Chem., 66, pp. 8859-8866 
504 |a Iriarte Capaccio, C.A., Varela, O., (2002) J. Org. Chem., 67, pp. 7839-7846 
504 |a The α and β descriptors were employed to indicate that the addition of the diene to the (2S)-dihydropyranone ring took place from the opposite (α) or the same side (β) respect to the 2-alkoxy substituent; note; note; Fratiello, A., Schuster, R.E., (1972) J. Org. Chem., 37, pp. 2237-2241 
504 |a Childs, R.F., Mulholland, D.L., Nixon, A., (1982) Can. J. Chem., 60, pp. 801-808 
504 |a Bonnesen, P.V., Puckett, C.L., Honeychuck, R.V., Hersh, W.H., (1989) J. Am. Chem. Soc., 111, pp. 6070-6081 
504 |a Faller, J.W., Ma, Y., (1991) J. Am. Chem. Soc., 113, pp. 1579-1586 
504 |a 1a with Lewis acids: for the 1H NMR experiments, the dihydropyranone 1a (10 mg) was dissolved in CDCl3 (0.6 mL) in a NMR tube and cooled to -78°C. The number of molar equivalents of the Lewis acid indicated in Table 2 were added. The solution was stirred and allowed to reach room temperature to register the spectrum. Compound 1a was stable at temperatures between -20 and 20°C, for times longer than those required for the acquisition of the spectrum; Halpern, Y., Riffer, R., Broido, A., (1973) J. Org. Chem., 38, pp. 204-209 
504 |a Shafizadeh, F., Chin, P.P.S., (1977) Carbohydr. Res., 58, pp. 79-87 
504 |a Dewar, M.J.S., Zoebisch, E.G., Healy, E.F., Stewart, J.J.P., (1985) J. Am. Chem. Soc., 107, pp. 3902-3909 
504 |a Dauben, W.G., Kowalczyk, B.A., Lichtenthaler, F.W., (1990) J. Org. Chem., 55, pp. 2391-2398 
504 |a Reetz, M.T., Westermann, J., (1981) Synth. Commun., 11, pp. 647-654 
504 |a Dawoodi, Z., Green, M.L.H., Mtetwa, V.S.B., Prout, K., (1982) J. Chem. Soc., Chem. Commun., pp. 802-803 
504 |a Reetz, M.T., Kesseler, K., Jung, A., (1984) Tetrahedron, 40, pp. 4327-4336 
504 |a Castellino, S., (1990) J. Org. Chem., 55, pp. 5197-5200 
520 3 |a The influence of such Lewis acids as Et2O·BF3, ZnCl2, SnCl4 and TiCl4 on the stereochemical course of the Diels-Alder cycloadditions of sugar-derived (2S)-alkoxydihydropyranones was studied. The first two catalysts promoted the addition of dienes to give (3S,4aR,8aS)-3-alkoxy-4a,5,8,8a-tetrahydro-2-benzopyran-4-ones, and their concentration had almost no effect on the stereochemistry of the reaction. In contrast, the concentration of SnCl4 and TiCl4 had a remarkable influence on the selectivity, and even facial stereoselection reversal has been observed. These results may be ascribed to chelate complexation of the Lewis acid with the carbonyl and the vicinal alkoxy group of the dihydropyranone. © 2003 Elsevier Science Ltd. All rights reserved.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires, TX108 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: This work was supported by grants from the University of Buenos Aires (Project TX108) and the National Research Council of República Argentina (CONICET). O.V. is a Research Member of CONICET. 
593 |a CIHIDECAR-CONICET, Depto. de Quím. Orgán., Pabellón II, 1428 Buenos Aires, Argentina 
690 1 0 |a ALKADIENE 
690 1 0 |a CARBOHYDRATE DERIVATIVE 
690 1 0 |a CHELATE 
690 1 0 |a LEWIS ACID 
690 1 0 |a PYRAN DERIVATIVE 
690 1 0 |a TIN DERIVATIVE 
690 1 0 |a TITANIUM DERIVATIVE 
690 1 0 |a ZINC DERIVATIVE 
690 1 0 |a ARTICLE 
690 1 0 |a CATALYST 
690 1 0 |a CHEMICAL REACTION 
690 1 0 |a CONCENTRATION (PARAMETERS) 
690 1 0 |a CYCLOADDITION 
690 1 0 |a DIELS ALDER REACTION 
690 1 0 |a PROTON NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a BETULACEAE 
700 1 |a Varela, O. 
773 0 |d Elsevier Ltd, 2003  |g v. 44  |h pp. 4023-4026  |k n. 21  |p Tetrahedron Lett.  |x 00404039  |w (AR-BaUEN)CENRE-415  |t Tetrahedron Letters 
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