Artículos de revistas
Synthesis Of α-alkenyl-α-amino Esters Via Addition Of Potassium Alkenyltrifluoroborate Salts To Imine In The Presence Of Yb(otf)3
Registro en:
Tetrahedron Letters. , v. 54, n. 46, p. 6204 - 6207, 2013.
404039
10.1016/j.tetlet.2013.08.133
2-s2.0-84885483816
Autor
Stefani H.A.
Khan A.N.
Manarin F.
Vendramini P.H.
Eberlin M.N.
Institución
Resumen
A simple protocol which led to an effective construction of α-alkenyl-α-amino esters was achieved under mild conditions. This transformation proceeded by Yb-catalyzed addition of alkenyltrifluoroborates across the imine double bond. A variety of functional groups could be applicable to both partners. © 2013 Elsevier Ltd. All rights reserved. 54 46 6204 6207 Berkowitz, D.B., Charette, B.D., Karukurichi, K.R., McFadden, J.M., (2006) Tetrahedron: Asymmetry, 17, p. 869 Rando, R.R., (1975) Acc. Chem. Res., 8, p. 281 Berkowitz, D.B., Jahng, W.J., Pedersen, M.L., (1996) Bioorg. Med. Chem. Lett., 6, p. 2151 Feng, L., Kirsch, J.F., (2000) Biochemistry, 39, p. 2436 Soper, T.S., Manning, J.M., Marcotte, P.A., Walsh, C.T., (1977) J. Biol. Chem., 252, p. 1571 Sahm, U., Knobloch, G., Wagner, F., (1973) J. Antibiot., 26, p. 389 Pruess, D.L., Scannell, J.P., Kellett, M., Ax, H.A., Janecek, J., Williams, T.H., Stempel, A., Berger, J., (1974) J. Antibiot., 27, p. 229 Kuroda, Y., Okuhara, M., Goto, T., Kohsaka, M., Aoki, H., Imanaka, H., (1980) J. Antibiot., 33, p. 132 Kand, D., Chauhan, D.P., Lahiri, M., Talukdar, P., (2013) Chem. Commun., p. 3591 Brak, K., Ellman, J.A., (2009) J. Am. Chem. Soc., 131, p. 3850 Luo, Y., Carnell, A.J., Lam, H.W., (2012) Angew. Chem., Int. Ed., 51, p. 6762 Chen, J., Lu, X., Lou, W., Ye, Y., Jiang, H., Zeng, W., (2012) J. Org. Chem., 77, p. 8541 Li, Y., Xu, M.-H., (2012) Org. Lett., 14, p. 2062 Tremblay-Morin, J.-P., Raeppel, S., Gaudette, F., (2004) Tetrahedron Lett., 45, p. 3471 Matteson, D.S., (1995) Stereodirected Synthesis with Organoboranes, , Springer p 13 Pelter, A., Smith, K., Brown, H.C., (1988) Borane Reagents, , Academic Press London p. 187 Roy, C.D., Brown, H.C., (2007) Monatshefte für Chemie - Chemical Monthly, 138, p. 879 Darses, S., Genet, J.-P., (2007) Chem. Rev., 108, p. 288 Molander, G.A., Figueroa, R., (2005) Aldrichimica Acta, 38, p. 49 Stefani, H.A., Cella, R., Vieira, A.S., (2007) Tetrahedron, 63, p. 3623 Ji, J.X., Terry, T.L., Yeung, A., Wu, J., Yip, C.W., Chan, A.S.C., (2004) Adv. Synth. Catal., 346, p. 42 Payette, J.N., Yamamoto, H., (2008) J. Am. Chem. Soc., 130, p. 12276 Hong, K.B., Donahue, M.G., Johnston, J.N., (2008) J. Am. Chem. Soc., 130, p. 2323 Sun, S., Wu, P., (2010) J. Phys. Chem. A, 114, p. 8331 Matteson, D.S., Kim, G.Y., (2002) Org. Lett., 4, p. 2153 Curini, M., Epifano, F., Marcotullio, M.C., Rosati, O., (2002) Eur. J. Org. Chem., p. 1562