7 research outputs found
Stereoselective Arylation Of Substituted Cyclopentenes By Substrate-directable Heck-matsuda Reactions: A Concise Total Synthesis Of The Sphingosine 1-phosphate Receptor (s1p1) Agonist Vpc01091
We describe herein an efficient and diastereoselective substrate-directable Heck-Matsuda reaction with nonactivated five-membered olefins. The carbamate acts as the main directing group in the arylation process allowing the synthesis of several functionalized aryl cyclopentenes in good to excellent diastereoselectivities (>85:15) and in isolated yields ranging from 41 to 90%. No double bond isomerizations were observed in these Heck reactions, and the newly created benzylic centers were preserved in all cases examined. The substrate directable Heck arylation approach was successfully applied in a straightforward total synthesis of the sphingosine 1-phosphate receptor-subtype 1 (S1P1) agonist VPC01091 by a concise and practical route involving 5 steps in 40% overall yield. © 2012 American Chemical Society.771881828190Beletskaya, I.P., Cheprakov, A.V., (2000) Chem. Rev., 100, p. 3009Alonso, F., Beletskaya, I.P., Yus, M., (2005) Tetrahedron, 61, p. 11771Negishi, E.-I., (2002) Handbook of Organopalladium Chemistry for Organic Synthesis, , Wiley-Interscience: New YorkTsuji, J., (2004) Palladium Reagents and Catalyst, , Wiley: Chichester, U.KOestreich, M., (2009) The Mizoroki-Heck Reaction, , Wiley: Chichester, U.KRoglans, A., Pla-Quintana, A., Moreno-Manas, M., (2006) Chem. Rev., 106, p. 4622Taylor, J.G., Moro, A.V., Correia, C.R.D., (2011) Eur. J. Org. Chem., p. 1403Felpin, F.-X., Nassar-Hardy, L., Callonnec, F.L., Fouquet, E., (2011) Tetrahedron, 67, p. 2815Moro, A.V., Cardoso, F.S.P., Correia, C.R.D., (2009) Org. Lett., 11, p. 3642Prediger, P., Barbosa, L.F., Génisson, Y., Correia, C.R.D., (2011) J. Org. Chem., 76, p. 7737Hoveyda, A.H., Evans, D.A., Fu, G.C., (1993) Chem. Rev., 93, p. 1307Hodgson, D.M., Thompson, A.J., Wadman, S., Keats, C.J., (1999) Tetrahedron, (55), p. 10815Stewart, C., Keitz, B.K., Kuhn, K.M., Thomas, R.M., Grubbs, R.H., (2010) J. Am. Chem. Soc., 132, p. 8534Niwayama, S., Cho, H., Lin, C., (2008) Tetrahedron Lett., 49, p. 4434Lebel, H., Leogane, O., (2006) Org. Lett., 7, p. 4107Soldi, C., Moro, A.V., Pizzolatti, M.G., Correia, C.R.D., (2012) Eur. J. Org. Chem., p. 3607Nassar-Hardy, L., Fabre, S., Amer, A.M., Fouquet, E., Felpin, F.-X., (2012) Tetrahedron Lett., 53, p. 338Schwalm, C.S., De Castro, I.B.D., Ferrari, J., De Oliveira, F.L., AparÃcio, R., Correia, C.R.D., (2012) Tetrahedron Lett., 53, p. 1660Werner, E.W., Sigman, M.S., (2011) J. Am. Chem. Soc., 133, p. 9692Taylor, J.G., Correia, C.R.D., (2011) J. Org. Chem., 76, p. 857Da Penha, E.T., Forni, J.A., Biajoli, A.F.P., Correia, C.R.D., (2011) Tetrahedron Lett., 52, p. 6342Schmidt, B., Holter, F., Kelling, A., Schilde, U., (2011) J. Org. Chem., 76, p. 3357Taylor, J.G., Ribeiro, R.S., Correia, C.R.D., (2011) Tetrahedron Lett., 52, p. 3861De Azambuja, F., Correia, C.R.D., (2011) Tetrahedron Lett., 52, p. 42Siqueira, F.A., Taylor, J.G., Correia, C.R.D., (2010) Tetrahedron Lett., 51, p. 2102Correia, C.R.D., Oliveira, C.C., Salles Jr., A.G., Dos Santos, E.A.F., (2012) Tetrahedron Lett., 53, p. 3325Kikukawa, K., Matsuda, T., (1977) Chem. Lett., p. 159Kikukawa, K., Maemura, K., Nagira, K., Wada, F., Matsuda, T., (1980) Chem. Lett., p. 551Kikukawa, K., Nagira, K., Wada, F., Matsuda, T., (1981) Tetrahedron, 37, p. 31Sengupta, S., Bhattacharya, S., (1993) J. Chem. Soc. Perkin Trans. 1, 17, p. 1943Colas, C., Goeldner, M., (1999) Eur. J. Org. Chem., p. 1357Salabert, J., Sebstián, R.M., Vallribera, A., Roglans, A., Nájera, C., (2011) Tetrahedron., 45, p. 8659Pla-Quintana, A., Parella, T., Roglans, A., (2011) Adv. Synth. Catal., 353, p. 2003Artuso, E., Barbero, M., Degani, I., Dughera, S., Fochi, R., (1981) Tetrahedron, 37, p. 31Nelson, M.L., Ismail, M.Y., McIntyre, L., Bhatia, B., Viski, P., Hawkins, P., Rennie, G., Levy, S.B., (2003) J. Org. Chem., 68, p. 5838Peñafiel, I., Pastor, I.M., Yus, M., (2012) Eur. J. Org. Chem., p. 3151Larue, V., Gharbi-Benarous, J., Acher, F., Valle, G., Crisma, M., Toniolo, C., Azerad, R., Girault, J.-P., (1995) J. Chem. Soc., Perkin Trans., 2, p. 1111Ung, A.T., Pyne, S.G., Batenburg-Nguyen, U., Davis, A.S., Sherif, A., Biscoff, F., Lesage, A.S.J., (2005) Tetrahedron, 61, p. 1803Lynch, K.R., MacDonald, T.L., (2006) Sphingosine 1-Phosphate Agonists Comprising Cycloalkanes and 5-Membered Heterocycles Substituted by Amino and Phenyl Groups, , WO Patent 2006088944Zhu, R., Snyder, A.H., Kharel, Y., Schaffter, L., Sun, Q., Kennedy, P.C., Lynch, K.R., MacDonald, T.L., (2007) J. Med. Chem., 50, p. 6428Fix-Stenzel, S.R., Hayes, M.E., Zhang, X., Wallace, G.A., Grongsaard, P., Schaffter, L.M., Hannick, S.M., Cusack, K.P., (2009) Tetrahedron Lett., 50, p. 4081Wallace, G.A., Gordon, T.D., Hayes, M.E., Konopacki, D.B., Fix-Stenzel, S.R., Zhang, X., Grongsaard, P., Stoffel, R.H., (2009) J. Org. Chem., 74, p. 4886Strader, C.R., Pearce, C.J., Oberlies, N.H., (2011) J. Nat. Prod., 74, p. 900Nakano, T., Miyahara, M., Itoh, T., Kamimura, A., Eur. J. Org. Chem., 2012, p. 2161Lewis, N., McKillop, A., Taylor, R.J.K., Watson, R.J., (1995) Synth. Commun., 25, p. 561Moro, A.V., Santos, M.R., Correia, C.R.D., (2011) Eur. J. Org. Chem., p. 7259Singh, R., Just, G., (1989) J. Org. Chem., 54, p. 4453Denmark, S.E., Thorarensen, A., Middleton, D.S., (1996) J. Am. Chem. Soc., 118, p. 8266Still, W.C., Kahn, M., Mitra, A., (1978) J. Org. Chem., 43, p. 2923Plé, K., Haudrechy, A., Probst, N.P., (2010) Tetrahedron, 66, p. 5030Dunker, M.F.W., Starkey, E.B., Jenkins, G.L., (1936) J. Am. Chem. Soc., 58, p. 2308Starkey, E.B., (1943) Org. Synth., 2, p. 22