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84981510257
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Rueping recently reported this cyclization type using a visible-light photoredox process c
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Rueping recently reported this cyclization type using a visible-light photoredox process: c) E. Fava, M. Nakajima, M. B. Tabak and M. Rueping, Green Chem., 2016, 18, 4531–4535;
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iron-catalyzed redox radical cyclization of 1,6-dienes f
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iron-catalyzed redox radical cyclization of 1,6-dienes: f) T. Taniguchi, N. Goto, A. Nishibata and H. Ishibashi, Org. Lett., 2010, 12, 112–115;
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cyclization of cyclohexene-tethered 2-enynamides using Fe
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cyclization of cyclohexene-tethered 2-enynamides using FeX2: h M.-C. P. Yeh, Y.-S. Shiue, H.-H. Lin, T.-Y. Yu, T.-C. Hu, J.-J. Hong, Org. Lett. 2016, 18, 2407–2410.
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For a synthesis of enamides through the acylation of imines with haloacetyl chlorides, see a
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A. J. Clark, D. P. Curran, D. J. Fox, F. Ghelfi, C. S. Guy, B. Hay, N. James, J. M. Phillips, F. Roncaglia, P. B. Sellars, P. Wilson and H. Zhang, J. Org. Chem., 2016, 81, 5547–5565.
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0037047541
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For the radical cyclization of analogous haloacetamides leading to 3-unsubstituted hydroindoles, see a
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For the stereochemical elucidation of, cis, trans, -octahydroindoles, se
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Wille, U.1
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26
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85018869909
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The noncyclized allyl derivative shown below was also isolated in 30 % yield
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The noncyclized allyl derivative shown below was also isolated in 30 % yield.
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-
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27
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0022495270
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G. Stork, P. M. Sher and H.-L. Chen, J. Am. Chem. Soc., 1986, 108, 6384–6385.
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85099674628
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We also observed that when using Bu, SnH that had been stored for a long time, a mixture of, cis, - and, trans, -hydroindoles 8 and 9 was isolated
-
3SnH that had been stored for a long time, a mixture of cis- and trans-hydroindoles 8 and 9 was isolated.
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-
-
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30
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84935009621
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1,5-Enynes allow five-membered-ring formation through gold-catalyzed 5-, endo, dig, cycloisomerizations a
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1,5-Enynes allow five-membered-ring formation through gold-catalyzed 5-endo-dig cycloisomerizations: a R. Dorel and A. M. Echavarren, Chem. Rev., 2015, 115, 9028–9072
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0041336779
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for regioselective 6-, endo, dig, cyclizations of, N, -propargylenamine derivatives using gold- and rhodium-catalyzed reactions, see b
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for regioselective 6-endo-dig cyclizations of N-propargylenamine derivatives using gold- and rhodium-catalyzed reactions, see: b G. Abbiati, A. Arcadi, G. Bianchi, S. Di Giuseppe, F. Marinelli and E. Rossi, J. Org. Chem., 2003, 68, 6959–6866;
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33
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0345363299
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For the cyclization of tethered alkyne enamides in a 5-, exo, process, see a
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For the cyclization of tethered alkyne enamides in a 5-exo process, see: a B. Alcaide, I. M. Rodríguez-Campos, J. Rodríguez-López and A. Rodríguez-Vicente, J. Org. Chem., 1999, 64, 5377–5387
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34
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85018894683
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b) ref.[4g
-
ref.[4g]
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-
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35
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84873350650
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For tethered alkyne imines, se
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For tethered alkyne imines, see: J. A. Pigza, J.-S. Han, A. Chandra, D. Mutnick, M. Pink and J. N. Johnston, J. Org. Chem., 2013, 78, 822–843.
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Pigza, J.A.1
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36
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84989031200
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For a discussion of the NMR spectroscopic data of (, Z, E,) rotamers in nitrogen-containing rings with an exocyclic amide group of a carbamate functionality, see a
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For a discussion of the NMR spectroscopic data of (Z)/(E) rotamers in nitrogen-containing rings with an exocyclic amide group of a carbamate functionality, see: a N. Valls, V. M. Segarra and J. Bonjoch, Magn. Reson. Chem., 1991, 29, 985–992;
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N. Valls, M. López-Canet, M. Vallribera and J. Bonjoch, Chem. Eur. J., 2001, 7, 3446–3460.
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Valls, N.1
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38
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0032541620
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For the analysis of coupling constants in, H NMR spectra of substituted cyclopentanes, se
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For the analysis of coupling constants in 1H NMR spectra of substituted cyclopentanes, see: G. M. Constantino and G. V. J. da Silva, Tetrahedron, 1998, 54, 11363–11374.
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Constantino, G.M.1
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39
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85018933195
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Rueping has observed that when 4,4-disubstituted aminocyclohexenes react to give 5,5-disubstituted octahydroindoles, the process takes place with lower yields than with other types of substrates under the same reaction conditions, 4c
-
Rueping has observed that when 4,4-disubstituted aminocyclohexenes react to give 5,5-disubstituted octahydroindoles, the process takes place with lower yields than with other types of substrates under the same reaction conditions.[4c]
-
-
-
-
40
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85018897097
-
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For the influence of the halogen atom on the 5-endo radical cyclization of haloacetamides to give octahydroindoles, see ref.[6b
-
For the influence of the halogen atom on the 5-endo radical cyclization of haloacetamides to give octahydroindoles, see ref.[6b]
-
-
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42
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70450159682
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for 3-methyl-, trans, -octahydroindol-2-ones, see also b
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for 3-methyl-trans-octahydroindol-2-ones, see also: b W. J. Nodes, D. R. Nutt, A. M. Chippindale, A. J. A. Cobb, J. Am. Chem. Soc. 2009, 131, 16016–16017.
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Nodes, W.J.1
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Cobb, A.J.A.4
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43
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85099673806
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H NMR (400 MHz, CDCl, = 1.84 (tt,, J, = 6.8, 1.2 Hz, 2 H), 1.90 (tt,, J, = 7.2, 0.8 Hz, 2 H), 2.29 (t,, J, = 2.4 Hz, 1 H), 2.48 (m, 4 H), 4.00 (s, 4 H), 4.26 (d,, J, = 2.4 Hz, 2 H) ppm
-
3): δ = 1.84 (tt, J = 6.8, 1.2 Hz, 2 H), 1.90 (tt, J = 7.2, 0.8 Hz, 2 H), 2.29 (t, J = 2.4 Hz, 1 H), 2.48 (m, 4 H), 4.00 (s, 4 H), 4.26 (d, J = 2.4 Hz, 2 H) ppm.
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