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(a) Fluoroorgunic Chemistry: Synthetic Challenges and Biomedical Rewards; Resnati, G., Soloshonok, V. A., Eds.; Tetrahedron Symposia-in-Print No 58; Tetrahedron 1996, 52, 1-330.
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Current methods for the asymmetric synthesis of trifluoromethylated amines rely on resolution of diastereomeric salts: (a) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2436-2439.
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Diastereoselective addition of aryl groups to chiral oxazolidines: (c) Ishii, A.; Miyamoto, F.; Higashiyama, K.; Mikami, K. Chem. Lett. 1998, 119-120. (d) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381-1382.
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3TMS to (tert-butylsulfinyl) imines: (g) Surya Prakash, G. K.; Mandai, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (h) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850.
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3TMS to (tert-butylsulfinyl) imines: (g) Surya Prakash, G. K.; Mandai, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590. (h) Surya Prakash, G. K.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847-2850.
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Perfluorinated ketones were prepared according to: Creary, X. J. Org. Chem. 1987, 52, 5026-5030.
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Creary, X.1
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26
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85039472807
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note
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3OD) δ -72.0.
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27
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0032541271
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Reviewed in: Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
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Corey, E.J.1
Helal, C.J.2
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28
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0346267223
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Oxazaborolidine catalysts were prepared according to: Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Turner Jones, E. T.; Hoogsteen, K.; Baum, M. W.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 751-762
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Mathre, D.J.1
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Xavier, L.C.3
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Reamer, R.A.5
Mohan, J.J.6
Turner Jones, E.T.7
Hoogsteen, K.8
Baum, M.W.9
Grabowski, E.J.J.10
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29
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0031656073
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For oxazaborolidine-mediated stoichiometric reductions of N-TMS imines: Ortiz-Marciales, M.; Tirado, L. M.; Colón, R.; Ufret, M. L.; Figueroa, R.; Lebrón, M.; Dejesus, M.; Martínez, J.; Malavé, T. Synth. Commun. 1998, 28, 4067-4075.
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Ortiz-Marciales, M.1
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Colón, R.3
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Figueroa, R.5
Lebrón, M.6
Dejesus, M.7
Martínez, J.8
Malavé, T.9
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0035855979
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3-substituted oxime ethers: (b) Demir, A. S.; Sesenoglu, Ö.; Gerçek-Arkin, Z. Tetrahedron: Asymmetry 2001, 12, 2309-2313.
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Demir, A.S.1
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Gerçek-Arkin, Z.3
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32
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85039475575
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note
-
3Br [M + H] 253.9792, found 253.9790.
-
-
-
-
33
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85039480742
-
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note
-
D = +11.2 (c = 1.5, MeOH).
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-
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34
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85039468641
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note
-
For example enantioselective reduction of N-H imine 7 with 5 mol % of commercially available (R)-methyl-OAB afforded amine (S)-14c in 90-91% ee on a 10 g scale. See Supporting Information.
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35
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0026480730
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Corey, E. J.; Link, J. O.; Bakshi, R. K. Tetrahedron Lett. 1992, 33, 7107-7110.
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Corey, E.J.1
Link, J.O.2
Bakshi, R.K.3
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36
-
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85039477071
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note
-
In a single unoptimized experiment we observed that isolated methanol adduct 7c containing less than 5% N-H imine underwent enantioselective reduction with (S)-methyl-OAB and catecholborane in toluene at -15°C to afford amine 14c in 72% yield and 78% ee.
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