-
4
-
-
85045847104
-
-
Cui C B., Kakeya H, Osada H, J. Antibiot. 1996 49 832
-
J. Antibiot.
, vol.49
, pp. 832
-
-
Cui, C.B.1
Kakeya, H.2
Osada, H.3
Cui, C.-B.4
Kakeya, H.5
Ckada, H.6
-
8
-
-
0033577262
-
-
Edmondson S, Danishefsky S J., Sepp-Lorenzino L, Rosen N, J. Am. Chem. Soc. 1999 121 2147
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 2147
-
-
Edmondson, S.1
Danishefsky, S.J.2
Sepp-Lorenzino, L.3
Rosen, N.4
-
9
-
-
0001030407
-
-
Jossang A, Jossang P, Hadi H A., Sevenet T, Bodo B, J. Org. Chem. 1991 56 6527
-
(1991)
J. Org. Chem.
, vol.56
, pp. 6527
-
-
Jossang, A.1
Jossang, P.2
Hadi, H.A.3
Sevenet, T.4
Bodo, B.5
-
11
-
-
0000587802
-
-
Bascop S, Sapi J, Laronze J, Levy J, Heterocycles 1994 38 725
-
(1994)
Heterocycles
, vol.38
, pp. 725
-
-
Bascop, S.1
Sapi, J.2
Laronze, J.3
Levy, J.4
-
13
-
-
0030032914
-
-
Palmisano G, Annunziata R, Papeo G, Sisti M, Tetrahedron: Asymmetry 1996 7 1
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 1
-
-
Palmisano, G.1
Annunziata, R.2
Papeo, G.3
Sisti, M.4
-
14
-
-
0033525843
-
-
Lakshmaiah G, Kawabata T, Shang M, Fuji K, J. Org. Chem. 1999 64 1699
-
(1999)
J. Org. Chem.
, vol.64
, pp. 1699
-
-
Lakshmaiah, G.1
Kawabata, T.2
Shang, M.3
Fuji, K.4
-
16
-
-
0035861696
-
-
Cravotto G, Giovenzana G, Pilati T, Sisti M, Palmisano G, J. Org. Chem. 2001 66 8447
-
(2001)
J. Org. Chem.
, vol.66
, pp. 8447
-
-
Cravotto, G.1
Giovenzana, G.2
Pilati, T.3
Sisti, M.4
Palmisano, G.5
-
19
-
-
0037049180
-
-
Selvakumar N, Azhagan A M., Srinivas D, Krishna G G., Tetrahedron Lett. 2002 43 9175
-
(2002)
Tetrahedron Lett.
, vol.43
, pp. 9175
-
-
Selvakumar, N.1
Azhagan, A.M.2
Srinivas, D.3
Krishna, G.G.4
-
22
-
-
23044491532
-
-
Murphy J A., Tripoli R, Khan T A., Mali U W., Org. Lett. 2005 7 3287
-
(2005)
Org. Lett.
, vol.7
, pp. 3287
-
-
Murphy, J.A.1
Tripoli, R.2
Khan, T.A.3
Mali, U.W.4
-
27
-
-
33750346700
-
-
Pinto A, Neuville L, Retailleau P, Zhu J, Org. Lett. 2006 8 4927
-
(2006)
Org. Lett.
, vol.8
, pp. 4927
-
-
Pinto, A.1
Neuville, L.2
Retailleau, P.3
Zhu, J.4
-
28
-
-
34250838053
-
-
Pinto A, Neuville L, Retailleau P, Zhu J, Angew. Chem. Int. Ed. 2007 46 3291
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 3291
-
-
Pinto, A.1
Neuville, L.2
Retailleau, P.3
Zhu, J.4
-
30
-
-
7044235263
-
-
For general reviews on the domino process
-
For general reviews on the domino process, see:, Tietze L F., Chem. Rev. 1996 96 115
-
(1996)
Chem. Rev.
, vol.96
, pp. 115
-
-
Tietze, L.F.1
-
33
-
-
33846425354
-
-
Pinto A, Jia X, Neuville L, Zhu J, Chem. Eur. J. 2007 13 961
-
(2007)
Chem. Eur. J.
, vol.13
, pp. 961
-
-
Pinto, A.1
Jia, X.2
Neuville, L.3
Zhu, J.4
-
38
-
-
33846232749
-
-
For related domino palladium-catalyzed cyanation process, see
-
Schareina T, Zapf A, Magerlein W, Muller N, Beller M, Tetrahedron Lett. 2007 48 1087 For related domino palladium-catalyzed cyanation process, see:
-
(2007)
Tetrahedron Lett.
, vol.48
, pp. 1087
-
-
Schareina, T.1
Zapf, A.2
Magerlein, W.3
Muller, N.4
Beller, M.5
-
39
-
-
37049008699
-
-
Mariampillai B, Alliot J, Li M, Lautens M, J. Am. Chem. Soc. 2007 129 15372
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 15372
-
-
Mariampillai, B.1
Alliot, J.2
Li, M.3
Lautens, M.4
-
40
-
-
43549120314
-
-
For a general review on palladium-catalyzed cross-coupling involving metal cyanides, see
-
Cheng Y.-N, Duan Z, Yu L, Li Z, Zhu Y, Wu Y, Org. Lett. 2008 10 901 For a general review on palladium-catalyzed cross-coupling involving metal cyanides, see:
-
(2008)
Org. Lett.
, vol.10
, pp. 901
-
-
Cheng, Y.-N.1
Duan, Z.2
Yu, L.3
Li, Z.4
Zhu, Y.5
Wu, Y.6
-
43
-
-
0035838860
-
-
For reviews, see
-
Yu C, Liu B, Hu L, J. Org. Chem. 2001 66 5413 For reviews, see:
-
(2001)
J. Org. Chem.
, vol.66
, pp. 5413
-
-
Yu, C.1
Liu, B.2
Hu, L.3
-
50
-
-
72049092852
-
-
note
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Experimental Procedure: To a degassed solution of iodoanilide 14 (1.90 g, 3.29 mmol, 1.0 equiv) in DMF (16mL) were added K4Fe(CN)6-3H2O (306.0 mg, 0.72 mmol, 0.22 equiv), Na2CO3 (350.0 mg, 3.30 mmol, 1.0 equiv) and Pd(OAc)2 (22.0 mg, 0.1 mmol, 0.03 equiv). After being stirred at 120 °C under an argon atmosphere for 3 h, the reaction mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (SiO2, heptane-EtOAc, 95:5 →90:10) to give the corresponding oxindole 15 (0.94g, 60%) as a light orange solid. Compound 15: 1H NMR (500 MHz, CDCl3): d = 7.06 (d, J = 2.6 Hz, 1 H), 7.02 (d, J = 8.6 Hz, 1 H), 6.88 (dd, J = 8.6, 2.6 Hz, 1 H), 5.17 (d, J = 11.0 Hz, 1 H), 5.11 (d, J = 11.0 Hz, 1 H), 3.92 (d, J = 9.7 Hz, 1 H), 3.80 (s, 3 H), 3.73 (d, J = 9.7 Hz, 1 H), 3.62-3.51 (m, 2 H), 3.02 (d, J = 16.7 Hz, 1 H), 2.79 (d, J = 16.7 Hz, 1 H), 0.92 (t, J = 8.2 Hz, 2 H), 0.84 (s, 9 H), 0.00 (s, 3 H), -0.01 (s, 3 H), -0.03 (s, 9 H). 13C NMR (75 MHz, CDCl3): d = 175.4, 156.4, 135.4, 129.1, 116.2, 114.3, 111.2, 110.6, 69.9, 66.5, 66.1, 55.8, 51.9, 25.7, 21.7, 18.1, 17.7, -1.4, -5.6, -5.7. HRMS (ES+): m/z [M + Na]+ calcd for C24H40N2O4Si2Na: 499.2424; found: 499.2415.
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Such reduction product has been reported in a related domino Heck reaction recently
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Such reduction product has been reported in a related domino Heck reaction recently:, Ruck R T., Huffman M A., Kim M K., Shevlin M, Kandur W V., Davies I W., Angew. Chem. Int. Ed. 2008 47 4711
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 4711
-
-
Ruck, R.T.1
Huffman, M.A.2
Kim, M.K.3
Shevlin, M.4
Kandur, W.V.5
Davies, I.W.6
-
53
-
-
0000271946
-
-
Satoh T, Suzuki S, Suzuki Y, Miyagi Y, Imai Z, Tetrahedron Lett. 1969 4555
-
(1969)
Tetrahedron Lett.
, pp. 4555
-
-
Satoh, T.1
Suzuki, S.2
Suzuki, Y.3
Miyagi, Y.4
Imai, Z.5
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