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38849118710
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PCT Int. Appl. WO 2006104356
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(b) Lee, C.-S.; Koh, J. S.; Koo, K. D.; Kim, G. T.; Kim, K.-H.; Hong, S. Y.; Kim, S.; Kim, M.-J.; Yim, H. J.; Lim, D.; Kim, H. J.; Han, H. O.; Bu, S. C.; Kwon, O. H.; Kim, S. H.; Hur, G.-C.; Kim, J. Y.; Yeom, Z.-H.; Yeo, D.-J. PCT Int. Appl. WO 2006104356, 2006.
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20
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4 Davis' protocol (a) with slight modifications in the workup (b): (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13 and references cited therein,
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4 Davis' protocol (a) with slight modifications in the workup (b): (a) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13 and references cited therein,
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22
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(b) García Ruano, J. L.; Alemán, J.; Cid, M. B.; Parra, A. Org. Lett. 2005, 7, 179.
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23
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33750966348
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For reaction with nitroethane and transformations, see also: García Ruano, J. L.; López-Cantarero, J.; de Haro, T.; Alemán, J.; Cid, M. B. Tetrahedron 2006, 62, 12197.
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For reaction with nitroethane and transformations, see also: García Ruano, J. L.; López-Cantarero, J.; de Haro, T.; Alemán, J.; Cid, M. B. Tetrahedron 2006, 62, 12197.
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-
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24
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17244375162
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For a review article on the conjugate additions of nitroalkanes, see
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For a review article on the conjugate additions of nitroalkanes, see: Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.
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Ballini, R.1
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Petrini, M.5
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25
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38849191443
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We observed a similar behavior when the corresponding N-sulfonylnitroamine, obtained by oxidation of the corresponding N-sulfinylnitroamine 1a was subjected to Michael addition conditions.
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We observed a similar behavior when the corresponding N-sulfonylnitroamine, obtained by oxidation of the corresponding N-sulfinylnitroamine 1a was subjected to Michael addition conditions.
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26
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38849175124
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When we used nitroamine with a phenyl group (1b) as starting material, compound obtained from retro aza-Henry reaction turned out to be the main product under most of the conditions used.
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When we used nitroamine with a phenyl group (1b) as starting material, compound obtained from retro aza-Henry reaction turned out to be the main product under most of the conditions used.
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27
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38849098708
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For enantioselective Michael addition of nitro derivatives with cinchona alkaloids see for example a review article: Almaşi, D, Alonso, D. A, Nájera, C. Tetrahedron: Asymmetry 2007, 299
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For enantioselective Michael addition of nitro derivatives with cinchona alkaloids see for example a review article: Almaşi, D.; Alonso, D. A.; Nájera, C. Tetrahedron: Asymmetry 2007, 299.
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29
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38849197227
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SCX (Strong cation exchange) resin to effect catch and release purification.
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SCX (Strong cation exchange) resin to effect "catch and release" purification.
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30
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0034710496
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For another example of synthesis of piperidones from sylfinylimines, see
-
For another example of synthesis of piperidones from sylfinylimines, see: Davis, F. A.; Chao, B. Org. Lett. 2000, 17, 2623.
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(2000)
Org. Lett
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Davis, F.A.1
Chao, B.2
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31
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38849139968
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3 and then filtered through a sort pad of silica gel eluting with EtOAc. The formation of a 87/13 mixture of 5a and 5a′ supports that epimerization is taking place under these conditions.
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3 and then filtered through a sort pad of silica gel eluting with EtOAc. The formation of a 87/13 mixture of 5a and 5a′ supports that epimerization is taking place under these conditions.
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-
-
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32
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84985146137
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A similar strategy that also uses aza-Henry reaction and cyclization has been described to obtained racemic 5-nitro-6-substituted lactames: Bhagwatheeswaran, H; Gaur, S. P, Jain, P. C. Synthesis 1976, 615
-
A similar strategy that also uses aza-Henry reaction and cyclization has been described to obtained racemic 5-nitro-6-substituted lactames: Bhagwatheeswaran, H; Gaur, S. P.; Jain, P. C. Synthesis 1976, 615.
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33
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38849129116
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Although in most of the cases the amine has been previously passed through a SCX column, it has been proven that the yields of the final piperidones are similar when the reaction crudes are directly treated with NH3 in MeOH see note b in entry 2 of Table 2 and Scheme 3
-
3 in MeOH (see note b in entry 2 of Table 2 and Scheme 3).
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34
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0029065938
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(a) Watson, J. W.; Gonsalves, S. F.; Fossa, A. A.; McLea, S.; Seeger, T.; Obach, S.; Andrews, P. L. R. Br. J. Pharmacol. 1995, 115, 84.
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Fossa, A.A.3
McLea, S.4
Seeger, T.5
Obach, S.6
Andrews, P.L.R.7
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35
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0033622021
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(b) Zaman, S.; Woods, A. J.; Watson, J. W.; Reynolds, D. J. M.; Andrews, P. L. R. Neuropharmacology 2000, 39, 316.
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Reynolds, D.J.M.4
Andrews, P.L.R.5
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36
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2142758070
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(c) Datar, P.; Srivastava, S.; Coutinho, E.; Govil, G. Curr. Top. Med. Chem. 2004, 4, 75.
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Datar, P.1
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37
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0027186206
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(a) Desai, M. C.; Thadeio, P. F.; Lefkowitz, S. L. Tetrahedron Lett. 1993, 34, 5831.
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(1993)
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Desai, M.C.1
Thadeio, P.F.2
Lefkowitz, S.L.3
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39
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29544439946
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For some examples of asymmetric synthesis of CP-99,994, see: (a) Xu, X.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. Eur. J. 2006, 12, 466.
-
For some examples of asymmetric synthesis of CP-99,994, see: (a) Xu, X.; Furukawa, T.; Okino, T.; Miyabe, H.; Takemoto, Y. Chem. Eur. J. 2006, 12, 466.
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-
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40
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22744432715
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(b) Okada, A.; Shibuguchi, T.; Ohshima, T.; Masu, H.; Yamaguchi, K.; Shibasaki, M. Angew. Chem. Int. Ed. 2005, 44, 4564.
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Angew. Chem. Int. Ed
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Okada, A.1
Shibuguchi, T.2
Ohshima, T.3
Masu, H.4
Yamaguchi, K.5
Shibasaki, M.6
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41
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34848892701
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(c) Davis, F. A.; Zhang, Y.; Li, D. Tetrehedron Lett. 2007, 48, 7838.
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(2007)
Tetrehedron Lett
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, pp. 7838
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Davis, F.A.1
Zhang, Y.2
Li, D.3
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42
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0041302241
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For Michael addition of other nitro derivatives on this substrate, see
-
For Michael addition of other nitro derivatives on this substrate, see: Miyake, N.; Kitazume, T. J. Fluorine Chem. 2003, 122, 243.
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(2003)
J. Fluorine Chem
, vol.122
, pp. 243
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Miyake, N.1
Kitazume, T.2
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44
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38849150043
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For a discussion of the stereochemical assignment as well as some molecular modeling supporting such assignment, see the Supporting Information
-
For a discussion of the stereochemical assignment as well as some molecular modeling supporting such assignment, see the Supporting Information.
-
-
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45
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33644784912
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To prepare 7a and 7b, we followed the same procedure described for the synthesis of the corresponding t-Bu (Ellman) sulfinimine-ethanol adducts: Kuduk, S. D.; Di Marco, C. Ng.; Pitzenberger, S. M.; Tsou, N. Tetrahedron Lett. 2006, 47, 2377.
-
To prepare 7a and 7b, we followed the same procedure described for the synthesis of the corresponding t-Bu (Ellman) sulfinimine-ethanol adducts: Kuduk, S. D.; Di Marco, C. Ng.; Pitzenberger, S. M.; Tsou, N. Tetrahedron Lett. 2006, 47, 2377.
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