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Using iodine; (a) Tanner, D.; Sellén, M.; Bäckvall, J.-E. J. Org. Chem. 1989, 54, 3374-3378.
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34547396187
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Using NIS: (a) Blough, B. E, Mascarella, S. W, Rothman, R. B, Carroll, F. I. J. Chem. Soc, Chem. Commun. 1993, 758-760
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Using NIS: (a) Blough, B. E.; Mascarella, S. W.; Rothman, R. B.; Carroll, F. I. J. Chem. Soc., Chem. Commun. 1993, 758-760.
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9
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(a) Ferraz, H. M. C.; Pereira, F. L. C.; Leite, F. S.; Nunes, M. R. S.; Payret-Arrúa, M. E. Tetrahedron 1999, 55, 10915-10924.
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For the t-BuOI-promoted cyclization of N-alkenylamides: Minakata, S.; Morino, Y.; Oderaoroshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 3335-3337.
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(d) For the t-BuOI-promoted cyclization of N-alkenylamides: Minakata, S.; Morino, Y.; Oderaoroshi, Y.; Komatsu, M. Org. Lett. 2006, 8, 3335-3337.
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(c) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991-1994.
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(d) Bubnov, Y. N.; Misharin, M. A.; Ignatenko, A. V. Tetrahedron Lett. 1997, 38, 6259-6262.
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(f) Verhelst, S. H. L.; Martinez, B. P.; Timmer, M. S. M.; Lodder, G.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Org. Chem. 2003, 68, 9598-9603.
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(g) Davies, S. G.; Nicholson, R. L.; Price, P. D.; Roberts, P. M.; Smith, A. D. Synlett 2004, 901-903.
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(h) Kim, J. H.; Long, M. J. C.; Deo, W. D.; Ryu, Y. B.; Yang, M. S.; Park, K. H. J. Org. Chem. 2005, 70, 4082- 4087.
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(i) Fiorelli, C.; Marchioro, C.; Martelli, G.; Monari, M.; Savoia, D. Eur. J. Org. Chem. 2005, 3987-3993.
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Inter alia, see: a
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Inter alia, see: (a) Tamaru, Y.; Kawamura, S.; Tanaka, K.; Yoshida, Z. Tetrahedron Lett. 1984, 25, 1063-1066.
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26
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(b) Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc, Perkin Trans. 1 2001, 2874-2883.
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(e) Davis, F. A.; Song, M.; Augustine, A. J. Org. Chem. 2006, 71, 2779-2786.
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Davis, F.A.1
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30
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-
29144468045
-
-
Of the cyclohexylamines 3a-c and 4a-c here described, only 3a has been previously reported. This amine has been prepared by an enantioselective reduction of imine 2a: Ros, A.; Magriz, A.; Dietrich, H.; Ford, M.; Fernández, R.; Lassaletta, J. M. Adv. Synth. Catal. 2005, 347, 1917-1920.
-
Of the cyclohexylamines 3a-c and 4a-c here described, only 3a has been previously reported. This amine has been prepared by an enantioselective reduction of imine 2a: Ros, A.; Magriz, A.; Dietrich, H.; Ford, M.; Fernández, R.; Lassaletta, J. M. Adv. Synth. Catal. 2005, 347, 1917-1920.
-
-
-
-
31
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27144470285
-
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For a recent example of diastereoselective reduction of 2-substituted iminocyclohexanes, see
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For a recent example of diastereoselective reduction of 2-substituted iminocyclohexanes, see: Sanderson, J. M.; Findlay, J. B. C.; Fishwick, C. W. G. Tetrahedron 2005, 61, 11244-11252.
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Sanderson, J.M.1
Findlay, J.B.C.2
Fishwick, C.W.G.3
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32
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33845551193
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For a classic paper in this field
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For a classic paper in this field: Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412.
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Cistone, F.4
Stercho, Y.P.5
-
34
-
-
4544316937
-
-
10 For another procedure to achieve 3-alkyl-2-allylcyclohexylamines, starting from 2-cyclohexenone, see
-
( 10) For another procedure to achieve 3-alkyl-2-allylcyclohexylamines, starting from 2-cyclohexenone, see: Dijk, E. W.; Panella, L.; Pinho, P.; Naasz, R.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2004, 60, 9687-9693.
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Dijk, E.W.1
Panella, L.2
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Meetsma, A.5
Minnaard, A.J.6
Feringa, B.L.7
-
35
-
-
0032811082
-
-
For nucleophilic ring opening of bicyclic aziridinium ions, see: a
-
For nucleophilic ring opening of bicyclic aziridinium ions, see: (a) Cossy, J.; Dumas, C.; Pardo, D. G. Eur. J. Org. Chem. 1999, 1693-1699.
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Cossy, J.1
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(b) Graham, M. A.; Wadsworth, A. H.; Thornton-Pett, M.; Rayner, C. M. Chem. Commun. 2001, 966-967.
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39
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33847090061
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For a classical conformational and configurational study on cis-decahydroquinolines: Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1977, 42, 51-62.
-
For a classical conformational and configurational study on cis-decahydroquinolines: Vierhapper, F. W.; Eliel, E. L. J. Org. Chem. 1977, 42, 51-62.
-
-
-
-
40
-
-
33746876014
-
-
For the application of this protocol to the synthesis of cis-decahydroquinolines, see: Mena, M.; Bonjoch, J.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2006, 71, 5930-5935. Figure Presented
-
For the application of this protocol to the synthesis of cis-decahydroquinolines, see: Mena, M.; Bonjoch, J.; Gomez Pardo, D.; Cossy, J. J. Org. Chem. 2006, 71, 5930-5935. Figure Presented
-
-
-
-
41
-
-
17844396203
-
-
For a semiempirical MO approach to the mechanism of the NIS-mediated nucleophilic addition, see
-
For a semiempirical MO approach to the mechanism of the NIS-mediated nucleophilic addition, see: Mota, A. J.; Castellanos, E.; Alvarez de Cienfuegos, L.; Robles, R. Tetrahedron: Asymmetry 2005, 16, 1615-1629.
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Mota, A.J.1
Castellanos, E.2
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Robles, R.4
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43
-
-
0026029281
-
-
Interestingly, the aminocyclization of 2-allyl-N-tosylcyclohexylamines promoted by MCPBA oxidation always gives octahydroindole derivatives irrespective of the cis or trans relationship of the bishomoallylic amine used: Nuhrich, A.; Moulines, J. Tetrahedron 1991, 47, 3075-3088.
-
Interestingly, the aminocyclization of 2-allyl-N-tosylcyclohexylamines promoted by MCPBA oxidation always gives octahydroindole derivatives irrespective of the cis or trans relationship of the bishomoallylic amine used: Nuhrich, A.; Moulines, J. Tetrahedron 1991, 47, 3075-3088.
-
-
-
-
44
-
-
34547398776
-
-
Unlike 6, compounds 5 are conformationally heterogeneous at rt and showed very broad signals in their NMR spectra. Sharp and interpretable spectra of 5b were obtained at -20 °C.
-
Unlike 6, compounds 5 are conformationally heterogeneous at rt and showed very broad signals in their NMR spectra. Sharp and interpretable spectra of 5b were obtained at -20 °C.
-
-
-
-
45
-
-
0042670084
-
-
The NIS-promoted oxacyclization of frans-2-allylcyclohexanol gives an epimeric mixture of 2-iodomethylperhydrobenzofurane derivatives: Tanikaga, R.; Matsumoto, Y.; Sakaguchi, M.; Koyama, Y.; Ono, K. Tetrahedron Lett. 2003, 44, 6781-6783.
-
The NIS-promoted oxacyclization of frans-2-allylcyclohexanol gives an epimeric mixture of 2-iodomethylperhydrobenzofurane derivatives: Tanikaga, R.; Matsumoto, Y.; Sakaguchi, M.; Koyama, Y.; Ono, K. Tetrahedron Lett. 2003, 44, 6781-6783.
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46
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(a) Weinreb, S. M. Chem. Rev. 2006, 106, 2531-2549.
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(b) Schär, P.; Cren, S.; Renaud, P. Chimia 2006, 60, 131-141.
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Schär, P.1
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