| dc.creator | Burtoloso A.C.B. | |
| dc.creator | Correia C.R.D. | |
| dc.date | 2008 | |
| dc.date | 2015-06-30T19:24:16Z | |
| dc.date | 2015-11-26T14:30:07Z | |
| dc.date | 2015-06-30T19:24:16Z | |
| dc.date | 2015-11-26T14:30:07Z | |
| dc.date.accessioned | 2018-03-28T21:33:24Z | |
| dc.date.available | 2018-03-28T21:33:24Z | |
| dc.identifier | | |
| dc.identifier | Tetrahedron. , v. 64, n. 42, p. 9928 - 9936, 2008. | |
| dc.identifier | 404020 | |
| dc.identifier | 10.1016/j.tet.2008.08.001 | |
| dc.identifier | http://www.scopus.com/inward/record.url?eid=2-s2.0-50549094193&partnerID=40&md5=3ba28a2379c010344ff1cc5a4eddf650 | |
| dc.identifier | http://www.repositorio.unicamp.br/handle/REPOSIP/106086 | |
| dc.identifier | http://repositorio.unicamp.br/jspui/handle/REPOSIP/106086 | |
| dc.identifier | 2-s2.0-50549094193 | |
| dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1247021 | |
| dc.description | The stereoselective syntheses of cis conformationally constrained glutamate and aspartate analogues, containing an azetidine framework were accomplished from (S)-N-tosyl-2-phenylglycine in moderate overall yields. The key steps in these syntheses involved an efficient Wittig olefination of an azetidin-3-one, followed by a highly stereoselective rhodium catalyzed hydrogenation. The route could also be applied to the synthesis of a trans glutamate analogue, since epimerization of cis to trans isomer could be performed using DBU in toluene at reflux. © 2008 Elsevier Ltd. All rights reserved. | |
| dc.description | 64 | |
| dc.description | 42 | |
| dc.description | 9928 | |
| dc.description | 9936 | |
| dc.description | Kanai, Y., Smith, C.P., Hediger, M.A., (1993) Trends Neurosci., 16, p. 365 | |
| dc.description | Szatkowski, M., Attwell, D., (1994) Trends Neurosci., 17, p. 359 | |
| dc.description | Conn, P.J., Patel, J., (1994) The Metabotropic Glutamate Receptors, , Humana, Totowa/New Jersey, NJ pp 1-277 | |
| dc.description | Hollmann, M., Heinemann, S., (1994) Annu. Rev. Neurosci., 17, p. 31 | |
| dc.description | Nakanishi, S., (1994) Neuron, 13, p. 1031 | |
| dc.description | Nicolletti, F., Bruno, V., Copani, A., Casabona, G., Knöpfel, T., (1996) Trends Neurosci., 19, p. 267 | |
| dc.description | Daw, N.W., Stein, P.S., Fox, K.A., (1993) Rev. Neurosci., 16, p. 207 | |
| dc.description | Collingridge, G.L., Bliss, T.V.P., (1995) Trends Neurosci., 18, p. 54 | |
| dc.description | Cotman, C.W., Kahle, J.S., Miller, S.E., Ulas, J., Bridges, R.J., Excitatory Amino Acid Neurotransmission (1995) Psychopharmacology: The Fourth Generation of Progress, p. 75. , Bloom F.E., and Kupfer D.J. (Eds), Raven, New York, NY | |
| dc.description | Choi, D.W., (1990) Annu. Rev. Neurosci., 13, p. 171 | |
| dc.description | Meldrum, B.S., (1993) Brain Pathol., 3, p. 405 | |
| dc.description | Choi, D.W., (1994) Prog. Brain Res., 100, p. 47 | |
| dc.description | Rothman, S.M., Olney, J.W., (1995) Trends Neurosci., 18, p. 57 | |
| dc.description | Chamberlin, A.R., Bridges, R.J., Conformationally Constrained Amino Acids as Probes of Glutamate Receptors and Transporters (1993) Drug Design for Neuroscience, pp. 231-259. , Kozikowski A.P. (Ed), Raven, New York, NY | |
| dc.description | Kozikowski, A.P., Tückmantel, W., Reynolds, I.J., Wroblewski, T.J., (1990) J. Med. Chem., 33, p. 1561 | |
| dc.description | Kozikowski, A.P., Tückmantel, W., Liao, Y., Wroblewski, T.J., Wang, S., Pshenichkin, S., Surin, A., Thomsen, C., (1996) Bioorg. Med. Chem. Lett., 6, p. 2559 | |
| dc.description | Kozikowski, A.P., Tückmantel, W., Liao, Y., Wroblewski, T.J., Manev, H., Ikonomovic, S., (1993) J. Med. Chem., 36, p. 2706 | |
| dc.description | Bridges, R.J., Lovering, F.E., Humphrey, J.M., Stanley, M.S., Blakely, T.N., Cristofaro, M.F., Chamberlin, R., (1993) Bioorg. Med. Chem. Lett., 3, p. 115 | |
| dc.description | Arakawa, Y., Murakami, T., Arakawa, Y., Yoshifugi, S., (2003) Chem. Pharm. Bull., 51, p. 96 | |
| dc.description | De Kimpe, N., Boeykens, M., (1998) Tetrahedron, 54, p. 2619 | |
| dc.description | Hanessian, S., Bernstein, N., Yang, R., Maguire, R., (1999) Bioorg. Med. Chem. Lett., 9, p. 1437 | |
| dc.description | Couty, F., Evano, G., Rabasso, N., (2003) Tetrahedron: Asymmetry, 14, p. 2407 | |
| dc.description | Couty, F., Carlin-Sinclair, A., Rabasso, N., (2003) Synlett, p. 726 | |
| dc.description | Enders, D., Gries, J., (2005) Synthesis-Stuttgart, 20, p. 3508 | |
| dc.description | Kiss, L., Mangelinckx, S., Fülöp, F., DeKimpe, N., (2007) Org. Lett., 9, p. 4399 | |
| dc.description | Sivaprakasham, M., Couty, F., Evano, G., Srinivas, B., Sridhar, R., Rao, K.R., (2007) Arkivoc, 10, p. 71 | |
| dc.description | Gerona-Navarro, G., Angeles Bonache, M., Alías, M., Pérez de Vega, M.J., García-López, T., Pilar López, M., Cativiela, C., González-Muñiz, R., (2004) Tetrahedron Lett., 45, p. 2193 | |
| dc.description | Braüner-Osborne, H., Bunch, L., Chopin, N., Couty, F., Evano, G., Jensen, A.A., Kusk, M., Rabasso, N., (2005) Org. Biomol. Chem., 3, p. 3926 | |
| dc.description | Couty, F., Evano, G., (2006) Org. Prep. Proced. Int., p. 427 | |
| dc.description | Burtoloso, A.C.B., Correia, C.R.D., (2005) Synlett, p. 1559 | |
| dc.description | Burtoloso, A.C.B., Correia, C.R.D., (2004) Tetrahedron Lett., 45, p. 3355 | |
| dc.description | Burtoloso, A.C.B., Correia, C.R.D., (2005) J. Organomet. Chem., 690, p. 5636 | |
| dc.description | Dejaegher, Y., Kuz'nenok, N.M., Zvonok, A.M., De Kimpe, N., (2002) Chem. Rev., 102, p. 29. , For a review on azetidin-3-ones, see: | |
| dc.description | Pusino, A., Saba, A., Desole, G., (1985) Gazz. Chim. Ital., 115, p. 33. , Compound 4 was also prepared by Pusino: | |
| dc.description | Wang, J., Hou, Y., Wu, P., (1999) J. Chem. Soc., Perkin Trans. 1, p. 2277. , For the synthesis of N-tosyl-azetidin-3-ones employing Cu(acac)2, see: | |
| dc.description | For previous applications of the Wittig olefination of azetidin-3-ones, see:Hanessian, S., Fu, J., Chiara, J.L., Di Fabio, R., (1993) Tetrahedron Lett., 34, p. 4157 | |
| dc.description | Podlech, J., Seebach, D., (1995) Helv. Chim. Acta, 78, p. 1238 | |
| dc.description | Emmer, G., (1992) Tetrahedron, 48, p. 7165 | |
| dc.description | Liu, H., Ramani, B., (1985) Synth. Commun., 15, p. 965 | |
| dc.description | noteMatsuura, F., Hamada, Y., Shioiri, T., (1992) Tetrahedron Lett., 33, p. 7921 | |
| dc.description | noteClayden, J., Menet, C.J., Tchabanenko, K., (2002) Tetrahedron, 58, p. 4727 | |
| dc.description | Bergmeier, S.C., Seth, P.P., (1999) Tetrahedron Lett., 40, p. 6181 | |
| dc.description | Closson, W.D., Ji, S., Schulenberg, S., (1970) J. Am. Chem. Soc., 92, p. 650 | |
| dc.description | notenotePetasis, N., Bzowej, E.I., (1990) J. Am. Chem. Soc., 112, p. 6392 | |
| dc.description | Hanessian, S., Fu, J., (2001) Can. J. Chem., 79, p. 1812 | |
| dc.description | Masuda, K., Okutani, T., Kaneko, T., (1974) Chem. Pharm. Bull., 22, p. 1490 | |
| dc.description | Masuda, K., Okutani, T., (1974) Chem. Pharm. Bull., 22, p. 1498 | |
| dc.description | Marchand, A.P., Bartnik, R., (1997) Synlett, p. 1029 | |
| dc.description | noteJiang, J., Shah, H., Devita, R.J., (2003) Org. Lett., 5, p. 4101 | |
| dc.description | note | |
| dc.language | en | |
| dc.publisher | | |
| dc.relation | Tetrahedron | |
| dc.rights | fechado | |
| dc.source | Scopus | |
| dc.title | Stereoselective Synthesis Of Azetidine-derived Glutamate And Aspartate Analogues From Chiral Azetidin-3-ones | |
| dc.type | Artículos de revistas | |
