Artículos de revistas
An Easy And Efficient Method To Produce γ-amino Alcohols By Reduction Of β-enamino Ketones
Registro en:
Journal Of The Brazilian Chemical Society. , v. 15, n. 6, p. 971 - 975, 2004.
1035053
2-s2.0-12744281777
Autor
Harris M.I.N.C.
Braga A.C.H.
Institución
Resumen
Reduction of β-enamino ketones 2 with NaBH4 in glacial acetic acid gave γ-amino alcohols 1 in 70% to 98% yield with diastereomeric excesses, preferentially the syn product, from 44% to 90%. The stereochemistry of these compounds was confirmed by analysis of their tetrahydro-1,3-oxazine derivatives 3. 15 6 971 975 Gevorgyan, G.A., Agababian, G., (1984) Russ. Chem. Rev., 53, p. 581 Jäger, V., Buß, V., (1980) Liebigs Ann. Chem., p. 101 Wang, Y.F., Izawa, T., Kobayashi, S., Ohno, M., (1982) J. Am. Chem. Soc., 104, p. 6465 Heitsch, H., König, W.A., Decker, H., Bormann, C., Fiedler, H.P., Zähner, H., (1989) J. Antibiotics, 42, p. 711 Wovkulich, P.M., Uskokovic, M.R., (1981) J. Am. Chem. Soc., 103, p. 3956 Jäger, V., Schwab, W., Bub, V., (1981) Angew. Chem. Int. Ed. Engl., 20, p. 601 White, D.W., Gibbs, D.E., Verkade, J.G., (1979) J. Am. Chem. Soc., 101, p. 1937 Liguori, A., Romeo, G., Sindona, G., Ucella, N., (1988) Chem. Ber., 121, p. 105 Bongini, A., Cardillo, G., Orena, M., Porzi, G., Sandri, S., (1988) Chem. Lett., p. 87 Arisa, J., Font, J., Ortuño, R.M., (1990) Tetrahedron, 46, p. 1931 Narasaka, K., Ukaji, Y., Yamazaki, S., (1986) Bull. Chem. Soc. Jpn., 59, p. 525 Maroni, P., Gazaux, L., Tisnes, P., Zambeti, M., (1980) Bull. Soc. Chim. Fr. P II, p. 179 Matsumura, Y., Fujiwara, J., Maruoka, K., Yamamoto, H., (1983) J. Am. Chem. Soc., 105, p. 6312 Bartoli, G., Cimarelli, C., Palmieri, G., (1994) J. Chem. Soc., Perkin Trans. 1, p. 537 Bartoli, G., Cupone, G., Dalpozzo, R., De Nino, A., Maiuolo, L., Procopio, A., Tagarelli, A., (2002) Tetrahedron Lett., 43, p. 7441 Greenhill, J.V., (1977) Chem. Soc. Rev., 6, p. 277 Schuda, P.F., Ebner, C.B., Morgan, T.M., (1986) Tetrahedron Lett., 27, p. 2567 Barluenga, J., Aguilar, E., Fustero, S., Olano, B., Viado, A.L., (1992) J. Org. Chem., 57, p. 1219 Katritzky, A., Harris, P.A., (1990) Tetrahedron, 46, p. 987 Pilli, R.A., Russowsky, D., Dias, L.C., (1990) J. Chem. Soc., Perkin Trans. 1, p. 1213 Tramontini, M., (1982) Synthesis, p. 605 Gribble, G.W., Nutaitis, C.F., (1985) Org. Prep. Proc. Int., 17, p. 317 Gribble, G.W., (1998) Chem. Soc. Rev., 27, p. 395 Harris, M.I.N.C., (1993) PhD. Thesis, , Universidade Estadual de Campinas, Brazil Braga, A.C.H., Harris, M.I.N.C., CA, 128, p. 243740. , Br PI 9.502.467-0, 1995 noteBarluenga, J., Olano, B., Fustero, S., (1985) J. Org. Chem., 50, p. 4052