Artículos de revistas
Organocatalysis Reactions With Chiral Amines. Mechanistic Aspects And Use On Organic Synthesis [reações De Organocatálise Com Aminas Quirais. Aspectos Mecanísticos E Aplicações Em Síntese Orgânica]
Registro en:
Quimica Nova. , v. 32, n. 2, p. 469 - 481, 2009.
1004042
2-s2.0-66749084422
Autor
Amarante G.W.
Coelho F.
Institución
Resumen
The philosophy of organocatalysis is based on the utilization of organic compounds to catalyze organic transformations without the intervention of metals. This area has attracted much attention of the synthetic chemistry community on the last years, which can be confirmed by the explosion of published papers dealing with this subject. Phosphorus compounds, urea and thiourea derivatives, alkaloids, guanidine derivatives, for example, have already been used as organocatalysts. In this review we have focused on the use of chiral amines as organocatalyst. We have also chosen some outstanding examples to demonstrate the potentiality of this strategy in the synthesis of natural products and biologically active compounds. 32 2 469 481 Alexakis, A., (2007) Chimia, 61, p. 212 Hajos, Z.G., Parrish, D.R., (1974) J. Org. Chem, 39, p. 1615 Hajos, Z. G. Parrish, D. R. Patente Alemã DE 2,102,623,1978 (CA, 1978, 88, 62529)Eder, U., Sauer, G., Wiechert, R., (1971) Angew. Chem., Int. Ed, 10, p. 496 Eder, U. Sauer, G Wiechert, R. Patente Alemã DE 2014757, 1971 (CA, 1972, 76, 14180) Lohray, B. B. Curr. Science 2001, 81, 1519;List, B., Lerner, R.A., Barbas III, C.E., (2000) J. Am. Chem. Soc, 122, p. 2395 Para revisões em reações organocatalíticas, ver: Dalko, P. I. Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138;Dondoni, A., Massi, A., (2008) Angew. Chem., Int. Ed, 47, p. 4638 Gaunt, M.J., Johansson, C.C.C., McNally, A., Vo, N.T., (2007) Drug Disc. Today, 12, p. 8 List, B. Chem. Rev. 2007, 107, 5413 (número especial inteiramente dedicado à Organocatálise) Houk, K. N. List, B. Acc. Chem. Res. 2004, 37, 487 (número especial inteiramente dedicado à organocatálise assimétrica) Richmond, J. P. Adv. Synth. Catal. 2004, 346, 1007 (número especial inteiramente dedicado à organocatálise) Kocovsky, P. Malkov, A. V. Tetrahedron 2006, 62, 243 (número especial inteiramente dedicado ao uso de organocatálise em síntese orgânica)List, B., Yang, J.W., (2006) Science, 313, p. 1584 SciFinder - www.scifinder.com, acessada em Maio de 2008Danishefsky, S.J., Cain, P., (1976) J. Am. Chem. Soc, 98, p. 4975 Agami, C., Meynier, E., Puchot, C., Guilhem, J., Pascard, C., (1984) Tetrahedron, 40, p. 1031 Notz, W., List, B., (2000) J. Am. Chem. Soc, 122, p. 7386 Zhong, G., Hoffman, T., Lerner, R.A., Danishefsky, S.J., Barbas III, C.E., (1998) Angew. Chem., Int. Ed, 37, p. 2481 Zhong, G., Lerner, R.A., Barbas III, C.E., (1999) Angew. Chem., Int. Ed, 38, p. 3738 Hoang, L., Bahmanyar, S., Houk, K.N., List, B., (2003) J. Am. Chem. Soc, 125, p. 16 Martin, H., Bahmanyar, S., Houk, K.N., List, B., (2003) J. Am. Chem. Soc, 125, p. 2475 Bahmanyar, S., Houk, K.N., (2001) J. Am. Chem. Soc, 123, p. 11273 Bahmanyar, S., Houk, K.N., (2001) J.Am Chem. Soc, 123, p. 12911 Alleman, C., Gordillo, R., Clemente, E.R., Cheong, P.H.-Y., Houk, K.N., (2004) Acc. Chem. Res, 37, p. 558 Mase, N., Tanaka, E., Barbas III, C.E., (2003) Org. Lett, 5, p. 4369 Northrup, A.B., MacMillan, D.W., (2002) C J. Am. Chem. Soc, 124, p. 6798 Mase, N., Tanaka, E., Barbas III, C.E., (2004) Angew. Chem., Int. Ed, 43, p. 2420 Northrup, A.B., Mangion, I.K., Hettche, E., MacMllan, D.W.C., (2004) Angew. Chem., Int. Ed, 43, p. 2152 Northrup, A.B., MacMillan, D.W.C., (2004) Science, 305, p. 1752 Enders, D., Grondal, C., (2005) Angew. Chem., Int. Ed, 44, p. 1210 Enders, D., Palecek, J., Grondal, C., (2006) Chem. Commun, p. 655 Suri, J.E., Mitsumori, S., Albertshofer, K., Tanaka, E., Barbas III, C.E., (2006) J. Org. Chem, 71, p. 3822 Ramasastry, S.S.V., Zhang, H., Tanaka, E., Barbas III, C.E., (2007) J. Am. Chem. Soc, 129, p. 288 Ramasastry, S.S.V., Albertshofer, K., Utsumi, N., Tanaka, E., Barbas III, C.E., (2007) Angew. Chem., Int. Ed, 46, p. 5572 Li, H., Wang, B., Deng, L., (2006) J. Am. Chem. Soc, 128, p. 732 Mandal, T., Samanta, S., Zhao, C.-G., (2007) Org. Lett, 9, p. 943 Mannich, C., Krosche, W., (1912) Arch. Pharm, 250, p. 647 Para algumas revisões sobre essa reação veja: Kleinmann, E. E Em Comprehensive Organic Synthesis Trost, B. M. Flemming, I., eds. Pergamon Press: New York, 1991, 2, chapter 4.1;Arend, M., Westermann, B., Risch, N., (1998) Angew. Chem., Int. Ed, 37, p. 1044 Kobayashi, S., Ishitani, H., (1999) Chem. Rev, 99, p. 1069 Denmark, S., Nicaise, O.J.-C.E., (1999) Comprehensive Asymmetric Catalysis, 2, p. 93. , Jacobsen, E. N, Pfaltz, A.;Yamomoto, H, eds, Springer: Berlin (1997) Enantioselective Synthesis of α-Amino Acids, , Juaristi, E, ed.;Weinheim: Berlin Bergmeier, S.C., (2000) Tetrahedron, 56, p. 2561 Córdova, A., (2004) Acc. Chem. Res, 24, p. 102 Pellissier, H., (2006) Tetrahedron, 62, p. 2143 Friestad, G.K., Mathies, A.K., (2007) Tetrahedron, 63, p. 2541 List, B., (2000) J. Am. Chem. Soc, 122, p. 9336 List, B., Pojarliev, P., Biller, W.T., Martin, H., (2002) J. J. Am. Chem. Soc, 124, p. 827 Notz, W., Tanaka, E., Watanabe, S., Chowdari, N.S., Turner, J.M., Thayumanavan, R., Barbas III, C.E., (2003) J. Org. Chem, 68, p. 9624 Hayashi, Y., Tsuboi, W., Ashimine, I., Urushima, T., Shoji, M., Sakai, K., (2003) Angew. Chem., Int. Ed, 42, p. 3677 Bahmanyar, S., Houk, K.N., (2003) Org. Lett, 5, p. 1249 Bogevig, A., Juhl, K., Kumaragurubaran, N., Zhuang, W., Jorgensen, K.A., (2002) Angew. Chem., Int. Ed, 41, p. 1790 List, B., (2002) J. Am. Chem. Soc, 124, p. 5656 Zhong, G.A., (2003) Angew. Chem., Int. Ed, 42, p. 4247 Yang, J.W., Stadler, M., List, B., (2007) Angew. Chem., Int. Ed, 46, p. 609 Vesely, J., Rios, R., Ibrahem, I., Córdova, A., (2007) Tetrahedron Lett, 48, p. 421 Zhuang, W., Saaby, S., Jorgensen, K.A., (2004) Angew. Chem., Int. Ed, 43, p. 4476 Hotta, N., Touota, T., Matsuoka, K., Shigeta, Y., Kikkiwa, R., Kaneko, T., Takahashi, A., Sakamoto, N., (2001) Diabetes Care, 24, p. 1776 Chowdari, N.S., Ahmad, M., Albertshofer, K., Tanaka, E., Barbas III, C.E., (2006) Org. Lett, 8, p. 2839 Wu, P., Feldman, A.K., Nugent, A.K., Hawker, C.J., Scheel, A., Voit, B., Pyun, J., Fokin, V.V., (2004) Angew. Chem., Int. Ed, 43, p. 3928 Hayashi, Y., Urushima, T., Aratake, S., Okano, T., Obi, K., (2008) Org. Lett, 10, p. 21 Song, J., Shih, H.-W., Deng, L., (2007) Org. Lett, 9, p. 603 Ahrendt, K.A., Borths, C.J., MacMillan, D.W., (2000) C J. Am. Chem. Soc, 122, p. 4243 Jen, W.S., Wiener, J.J.M., MacMillan, D.W.C., (2000) J. Am. Chem. Soc, 122, p. 9874 Austin, J.E., MacMllan, D.W.C., (2002) J. Am. Chem. Soc, 124, p. 1172 List, B., (2006) Chem. Commun, p. 819 Halland, N., Aburel, P.S., Jorgensen, K.A., (2003) Angew. Chem., Int. Ed, pp. 43-661 Bartoli, G., Bosco, M., Carlone, A., Cavalli, A., Locatelli, M., Mazzanti, A., Ricci, P., Melchiorre, P., (2006) Angew. Chem., Int. Ed, 45, p. 4966 McCooey, S.H., Connon, S.J., (2007) Org. Lett, 9, p. 599 Albertshofer, K., Thayumanavan, R., Utsumi, N., Tanaka, E., Barbas III, C.E., (2007) Tetrahedron Lett, 48, p. 693 Mase, N., Thayumanavan, R., Tanaka, E., Barbas III, C.E., (2004) Org. Lett, 6, p. 2527 Reyes, E., Vicário, J.L., Badia, D., Carrilo, L., (2006) Org. Lett, 8, p. 6135 Xue, D., Chen, Y.-C., Wang, Q.-W., Cun, L.-E., Zhu, J., Deng, J.-G., (2005) Org. Lett, 7, p. 5293 Wang, J., Li, H., Zu, L., Wang, W., (2006) Org. Lett, 8, p. 1391 Wang, J., Li, H., Duan, W., Zu, L., Wang, W., (2005) Org. Lett, 7, p. 4713 Cao, Y.-J., Lai, Y.-Y., Wang, X., Li, Y.-J., Xiao, W.-J., (2007) Tetrahedron Lett, 48, p. 21 Tsogoeva, S.B., Wei, S., (2006) Chem. Commun, p. 1451 Liu, K., Cui, H.-E., Nie, J., Dong, K.-Y., Li, X.-J., Ma, J.-A., (2007) Org. Lett, 9, p. 923 Wei, S., Yalalov, D.A., Tsogoeva, S.B., Schmatz, S., (2007) Catal Today, 121, p. 151 Wilson, R.M., Jen, W.S., MacMillan, D.W., (2005) C J. Am. Chem. Soc, pp. 127-11616 Hagiwara, H., Kobayashi, K., Miya, S., Hoshi, T., Suzuki, T., Ando, M., Okamoto, T., Uda, H., (2002) J. Org. Chem, 67, p. 5969 Juhl, K., Jorgensen, K., (2003) A. Angew. Chem, 42, p. 1498. , Int. Ed Chow, S.S., Nevalainen, M., Evans, C.A., Johannes, C.W., (2007) Tetrahedron Lett, 48, p. 277 Austin, J.E., MacMillan, D.W., (2002) C J. Am. Chem. Soc, p. 124. , 12 Beeson, T.D., Mastracchio, A., Hong, J.-B., Ashton, K., MacMllan, D.W.C., (2007) Science, 316, p. 582 Jang, H.Y., Hong, J.B., MacMillan, D.W., (2007) C J. Am. Chem. Soc, 129, p. 7004 Kim, H., MacMillan, D.W., (2008) C J. Am. Chem. Soc, 130, p. 398 Morita, K., Suzuki, Z., Hirose, H., (1968) Bull Chem. Soc. Jpn, 41, p. 2815 Baylis, A. B. Hillman, M. E. D. DE 2155113, 1972 (CA 1972, 77, 434174) Basavaiah, D. Rao, P. D. Hyma, R. S. Tetrahedron 1996, 52, 8001;Ciganek, E., (1997) Organic Reactions, 51, pp. 201-350. , cap. 2, p Almeida, W.P., Coelho, E., (2000) Quim. Nova, 23, p. 98 Basavaiah, D., Rao, P.D., Satyanarayana, T., (2003) Chem. Rev, 103, p. 811 Para alguns exemplos do uso de adutos de Morita-Baylis-Hillman na síntese de produtos naturais e fármacos, ver: Amarante, G. W Rezende, P, Cavallaro, M, Coelho, E Tetrahedron Lett. 2008, 49, 3744;Silveira, G P. C Coelho, E Tetrahedron Lett. 2005, 46, All Coelho, E Rossi, R. C Tetrahedron Lett. 2002, 43, 2797;Mateus, C.R., Coelho, E., (2005) J. Braz. Chem. Soc, 16, p. 386 Masunari, A., Trazzi, G., Ishida, E., Coelho, E., Almeida, W.P., (2001) Synth. Commun, 31, p. 2127 Almeida, W.P., Coelho, E., (2003) Tetrahedron Lett, 44, p. 937 Hill, J.S., Isaacs, N.S., (1990) J. Phys. Org. Chem, 3, p. 285 Silva, L.S., Pavam, C.H., Almeida, W.P., Coelho, E., Eberlin, M.N., (2004) Angew. Chem, Int. Ed, 43, p. 4330 Santos, L.S., da Silveira Neto, B.A., Consorti, C.S., Pavam, C.H., Almeida, W.P., Coelho, E., Eberlin, M.N., Dupont, J., (2006) J. Phys. Org. Chem, 19, p. 731 Drewes, S.E., Freese, S.D., Emslie, N.D., Roos, G.H.P., (1988) Synth. Commun, 18, p. 1565 Markó, I.E., Giles, P.R., Hindley, N.J., (1997) Tetrahedron, 53, p. 1015 Iwabuchi, Y., Nakatani, M., Yokoyama, N., Hatakeyama, S., (1999) J. Am. Chem. Soc, 121, p. 10219 Nakano, A., Kawahara, S., Akamatsu, S., Morokuma, K., Nakatani, M., Iwabuchi, Y., Takahashi, K., Hatakeyama, S., (2006) Tetrahedron, 62, p. 381 Reetz, M.T., Mondière, R., Carballeira, J.D., (2007) Tetrahedron Lett, 48, p. 1679 Enders, D., Grondal, C., Hüttl, M.R.M., (2007) Angew. Chem., Int. Ed, 46, p. 1570 Ramachary, D.B., Chowdari, N.S., Barbas III, C.E., (2003) Angew. Chem., Int. Ed, 42, p. 4233 Ramachary, D.B., Barbas III, C.E., (2004) Chem. Eur. J, 10, p. 5323 Ramachary, D.B., Anebouselvy, K., Chowdari, N.S., Barbas III, C.E., (2004) J. Org. Chem, 69, p. 5838 Halland, N., Aburel, P.S., Jorgensen, K.A., (2004) Angew. Chem., Int. Ed, 43, p. 1272 Pulkkinen, J., Aburel, P.S., Halland, N., Jorgensen, K.A., (2004) Adv. Synth. Catal, 346, p. 1077 Huang, Y., Walji, A.M., Larsen, C.H., MacMllan, D.W., (2005) C J. Am. Chem. Soc, 127, p. 15051 Walji, A.M., MacMllan, D.W.C., (2007) Synlett, p. 1477 Enders, D., Hüttl, M.R.M., Grondal, C., Raabe, G., (2006) Nature, 441, p. 861 Enders, D., Huttl, M.R.M., Runsink, J., Raabe, G., Wendt, B., (2007) Angew. Chem., Int. Ed, 46, p. 467 (1988) Catalysis of Organic Reactions, , 1st ed, New York, cap.18