1,5-asymmetric Induction In The Boron-mediated Aldol Reactions Of β-oxygenated Methyl Ketones [indução Assimétrica 1,5-anti Na Adição De Enolatos De Boro De Metilcetonas β-oxigenadas A Aldeídos]

dc.creatorDias L.C.
dc.creatorAguilar A.M.
dc.date2007
dc.date2015-06-30T18:42:23Z
dc.date2015-11-26T14:32:07Z
dc.date2015-06-30T18:42:23Z
dc.date2015-11-26T14:32:07Z
dc.date.accessioned2018-03-28T21:35:28Z
dc.date.available2018-03-28T21:35:28Z
dc.identifier
dc.identifierQuimica Nova. , v. 30, n. 8, p. 2007 - 2015, 2007.
dc.identifier1004042
dc.identifier
dc.identifierhttp://www.scopus.com/inward/record.url?eid=2-s2.0-38949149334&partnerID=40&md5=bf5680b0060ab07f08d3af976e3b91ee
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/104430
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/104430
dc.identifier2-s2.0-38949149334
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1247529
dc.descriptionHigh levels of substrate-based 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of β-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate π-facial selectivity critically dependent upon the nature of the β-alkoxy protecting group. This 1,5-anti aldol methodology has been strategically employed in the total synthesis of several natural products. At present, the origin of the high level of 1,5-anti induction obtained with the boron enolates is unclear, although a model based on a hydrogen bonding between the alkoxy oxygen and the formyl hydrogen has been recently proposed.
dc.description30
dc.description8
dc.description2007
dc.description2015
dc.descriptionCowden, C.J., Paterson, I., (1997) Org. React, 51, p. 1
dc.descriptionSchetter, B., Mahrwald, R., (2006) Angew. Chem., Int. Ed, 45, p. 7506
dc.descriptionFranklin, A.S., Paterson, I., (1994) Contemp. Org. Synth, 1, p. 317
dc.descriptionPaterson, I.E., (1991) Comprehensive Organic Synthesis, 2, p. 301. , Heathcock, C. H, ed, Pergamon Press: New York
dc.descriptionEvans, D.A., Nelson, J.V., Taber, T.R., (1982) Top. Stereochem, 13, p. 1
dc.descriptionHeathcock, C. H. Em ref. 3, p. 181.
dc.descriptionKim, B. M.
dc.descriptionWilliams, S. F.
dc.descriptionMasamune, S. Em ref. 3, p. 239Correia Jr., I.R., Pilli, R.A., (2003) Quim. Nova, 26, p. 531
dc.descriptionPalomo, C., Oiarbide, M., García, J.M., (2004) Chem. Soc. Rev, 33, p. 65
dc.descriptionNorcross, R.D., Paterson, I., (1995) Chem. Rev, 95, p. 2041
dc.descriptionYeung, K.-S., Paterson, I., (2005) Chem. Rev, 105, p. 4237
dc.descriptionMengel, A., Reiser, O., (1999) Chem. Rev, 99, p. 1191
dc.descriptionZimmerman, H.E., Traxler, M.D., (1957) J. Am. Chem. Soc, 79, p. 1920
dc.descriptionEvans, D.A., Vogel, E., Nelson, J.V., (1979) J. Am. Chem. Soc, 101, p. 6120
dc.descriptionHoffmann, R.W., (1989) Chem. Rev, 89, p. 1841
dc.descriptionEvans, D.A., Rieger, D.L., Bilodeau, M.T., Urpí, F., (1991) J. Am. Chem. Soc, 113, p. 1047
dc.descriptionChérest, M., Felkin, H., Prudent, N., (1968) Tetrahedron Lett, 18, p. 2199
dc.descriptionAnh, N.T., Eisenstein, O., (1977) Nouv. J. Chem, 1, p. 61. , o termoFelkin referese ao diastereoisômero previsto pelo paradigma de Felkin-Ahn. O termo anti-Felkin refere-se aos diastereoisômeros não previstos por este modelo de indução
dc.descriptionPaterson, I., Goodman, J.M., (1989) Tetrahedron Lett, 30, p. 997
dc.descriptionPaterson, I., Florence, G.J., (2000) Tetrahedron Lett, 41, p. 6935
dc.descriptionBlanchette, M.A., Malamas, M.S., Nantz, M.H., Roberts, J.C., Somfai, P., Whritenour, D.C., Masamune, S., Tamura, T., (1989) J. Org. Chem, 54, p. 2817
dc.descriptionMasamune, S., Choy, W., Petersen, J.S., Sita, L.R., (1985) Angew. Chem., Int. Ed, 24, p. 1
dc.descriptionKolodiazhnyi, O.I., (2003) Tetrahedron, 59, p. 5953
dc.descriptionDenmark, S. E.
dc.descriptionAlmstead, N. G. Em Modern Carbonyl Chemistry
dc.descriptionOtera, J., ed.
dc.descriptionWiley-VCH: Weinheim: 2000, chapter 10Seebach, D., Prelog, V., (1982) Angew. Chem., Int. Ed, 21, p. 654
dc.descriptionMasamune, S., Hirama, M., Mori, S., Ali, S.K., Garvey, D.S., (1981) J. Am. Chem. Soc, 103, p. 1568
dc.descriptionDenmark, S.E., Fujimori, S., (2001) Synlett, p. 1024
dc.descriptionIzumi, Y., Tai, A., (1977) Stereodifferentiating Reactions: The Nature of Asymmetric Reactions, p. 533753. , Kodansha Limited: Tokyo. CAN 87:133753, AN, CAPLUS
dc.descriptionPaterson, I., Gibson, K.R., Oballa, R.M., (1996) Tetrahedron Lett, 37, p. 8585
dc.descriptionEvans, D.A., Coleman, P.J., Côté, B., (1997) J. Org. Chem, 62, p. 788
dc.descriptionEvans, D.A., Côté, B., Coleman, P.J., Connell, B.T., (2003) J. Am. Chem. Soc, 125, p. 10893
dc.descriptionPara investigações similares, ver: Evans, D. A.
dc.descriptionDart, M. J.
dc.descriptionDuffy, J. L.
dc.descriptionYang, M. G.
dc.descriptionJ. Am. Chem. Soc. 1996, 118, 4322;Gustin, D.J., VanNieuwenhze, M.D., Roush, W.R., (1995) Tetrahedron Lett, 36, p. 3443
dc.descriptionEvans, D.A., Trotter, B.W., Coleman, P.J., Côté, B., Dias, L.C., Rajapakse, H.A., Tyler, A.N., (1999) Tetrahedron, 55, p. 8671
dc.descriptionEvans, D.A., Trotter, B.W., Côté, B., Coleman, P.J., Dias, L.C., Tyler, A.N., (1997) Angew. Chem., Int. Ed, 36, p. 2744
dc.descriptionEvans, D.A., Trotter, B.W., Côté, B., Coleman, P.J., (1997) Angew. Chem., Int. Ed, 36, p. 2741
dc.descriptionEvans, D.A., Coleman, P.J., Dias, L.C., (1997) Angew. Chem., Int. Ed, 36, p. 2738
dc.descriptionEvans, D.A., Connell, B.T., (2003) J. Am. Chem. Soc, 125, p. 10899
dc.descriptionPaterson, I., Collett, L.A., (2001) Tetrahedron Lett, 42, p. 1187
dc.descriptionPaterson, I., Oballa, R.M., Norcross, R.D., (1996) Tetrahedron Lett, 37, p. 8581
dc.descriptionPaterson, I., Coster, M.J., Chen, D.Y.-K., Oballa, R.M., Wallace, D.J., Norcross, R.D., (2005) Org. Biomol. Chem, 3, p. 2399
dc.descriptionPaterson, I., Coster, M.J., Chen, D.Y.-K., Gibson, K.R., Wallace, D.J., (2005) Org. Biomol. Chem, 3, p. 2410
dc.descriptionPaterson, I., Coster, M.J., Chen, D.Y.-K., Aceña, J.L., Bach, J., Keown, L.E., Trieselmann, T., (2005) Org. Biomol. Chem, 3, p. 2420
dc.descriptionPaterson, I., Chen, D.Y.-K., Coster, M.J., Aceña, J.L., Bach, J., Wallace, D.J., (2005) Org. Biomol. Chem, 3, p. 2431
dc.descriptionDias, L.C., Baú, R.Z., de Sousa, M.A., Zukerman-Schpector, J., (2002) Org. Lett, 4, p. 4325
dc.descriptionPaterson, I., Goodman, J.M., Isaka, M., (1989) Tetrahedron Lett, 30, p. 7121
dc.descriptionDas, S., Li, L.-S., Sinha, S., (2004) Org. Lett, 6, p. 123
dc.descriptionArefolov, A., Panek, J.S., (2002) Org. Lett, 4, p. 2397
dc.descriptionArefolov, A., Panek, J.S., (2005) J. Am. Chem. Soc, 127, p. 5596
dc.descriptionPaterson, I., Tudge, M., (2003) Angew. Chem., Int. Ed, 42, p. 343
dc.descriptionPaterson, I., Tudge, M., (2003) Tetrahedron, 59, p. 6833
dc.descriptionDas, S., Abilaham, S., Sinha, S.C., (2007) Org. Lett, 9, p. 2273
dc.descriptionKozmin, S., (2001) Org. Lett, 3, p. 755
dc.descriptionEvans, D.A., Fitch, D.M., Smith, T.E., Cee, V.J., (2000) J. Am. Chem. Soc, 122, p. 10033
dc.descriptionPaterson, I., Di Francesco, M.E., Kühn, T., (2003) Org. Lett, 5, p. 599
dc.descriptionPaterson, I., Chen, D.Y.-K., Coster, M.J., Aceña, J.L., Bach, J., Gibson, K.R., Keown, L.E., Norcross, R.D., (2001) Angew. Chem., Int. Ed, 40, p. 4055
dc.descriptionPark, P.K., O'Malley, S.J., Schmidt, D.R., Leighton, J.L., (2006) J. Am. Chem. Soc, 128, p. 2796
dc.descriptionDias, L.C., Aguilar, A.M., Salles Jr., A.G., Steil, L.J., Roush, W.R., (2005) J. Org. Chem, 70, p. 10461
dc.descriptionDias, L.C., Aguilar, A.M., (2006) Org. Lett, 8, p. 4629
dc.descriptionRoush, W.R., Bannister, T.D., Wendt, M.D., VanNieuwenhze, M.S., Gustin, D.J., Dilley, G.J., Lane, G.C., Smith III, W.J., (2002) J. Org. Chem, 67, p. 4284
dc.descriptionLiu, C.M., Smith III, W.J., Gustin, D.J., Roush, W.R., (2005) J. Am. Chem. Soc, 127, p. 5770
dc.descriptionDias, L.C., Salles Jr., A.G., (2006) Tetrahedron Lett, 47, p. 2213
dc.descriptionLi, Y., Paddon-Row, M.N., Houk, K.N., (1988) J. Am. Chem. Soc, 110, p. 3684
dc.descriptionLi, Y., Paddon-Row, M.N., Houk, K.N., (1990) J. Org. Chem, 55, p. 481
dc.descriptionBernardi, A., Capelli, A.M., Gennari, C., Goodman, J.M., Paterson, I., (1990) J. Org. Chem, 55, p. 3576
dc.descriptionDiversos estudos computacionais indicam que os estados de transição do tipo cadeira e do tipo bote apresentam energias relativamente próximas em reações aldólicas com metilcetonas: Li, Y, Paddow-Row, M. N, Houk, K. N, J. Org. Chem. 1990, 55, 1535;Bernardi, F., Robb, M.A., Suzzi-Vall, G., Tagliavini, E., Trombin, C., Umani-Ronchi, A., (1991) J. Org. Chem, 56, p. 6472
dc.descriptionStocker, B.L., Teesdale-Spittle, P., Hoberg, J.O., (2004) Eur. J. Org. Chem, p. 330
dc.descriptionPaton, R.S., Goodman, J.M., (2006) Org. Lett, 8, p. 4299
dc.descriptionGoodman, J.M., Paton, R.S., (2007) Chem. Commun, 21, p. 24
dc.descriptionPara uma discussão das habilidades coordenantes de vários substituintes do tipo éter, ver: Reetz, M. T.
dc.descriptionAcc. Chem. Res. 1993, 26, 462;Chen, X.N., Hortellano, E.R., Eliel, E.L., Frye, S.V., (1990) J. Am. Chem. Soc, 112, p. 6130
dc.descriptionMori, S., Nakamura, M., Nakamura, E., Koga, N., Morokuma, K., (1995) J. Am. Chem. Soc, 117, p. 5055
dc.descriptionSchreiber, S.L., Shambayati, S., Blake, J.F., Wierschke, S.G., Jorgensen, W.L., (1990) J. Am. Chem. Soc, 112, p. 697
dc.languagept
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dc.relationQuimica Nova
dc.rightsaberto
dc.sourceScopus
dc.title1,5-asymmetric Induction In The Boron-mediated Aldol Reactions Of β-oxygenated Methyl Ketones [indução Assimétrica 1,5-anti Na Adição De Enolatos De Boro De Metilcetonas β-oxigenadas A Aldeídos]
dc.typeArtículos de revistas


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