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1
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For reviews that include methods for the synthesis of allylic amines, see: a
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For reviews that include methods for the synthesis of allylic amines, see: (a) Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1698-1708.
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62149147619
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Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2005; 66, pp 1-107. For examples of different methods for allylic amine synthesis, see:
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(c) Carpenter, N. E. In Organic Reactions; Overman, L. E., Ed.; Wiley: New York, 2005; Vol. 66, pp 1-107. For examples of different methods for allylic amine synthesis, see:
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(d) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761-768.
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(f) Yamashita, Y.; Gopalarathnam, A.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7508-7509.
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(g) Ngai, M.-Y.; Barchuk, A.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12644-12645.
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(h) Lalic, G.; Krinsky, J. L.; Bergman, R. G. J. Am. Chem. Soc. 2008, 130, 4459-4465.
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(i) Kinder, R. E.; Zhang, Z.; Widenhoefer, R. A. Org. Lett. 2008, 10, 3157-3159.
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Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Chem. Soc., Chem. Commun. 1978, 80-81.
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Sakurai, H.1
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Nakadaira, Y.3
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12
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0001363228
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For a related insertion of an imine, see
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For a related insertion of an imine, see: Seyferth, D.; Duncan, D. P.; Shannon, M. L. Organometallics 1984, 3, 579-583.
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(1984)
Organometallics
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Seyferth, D.1
Duncan, D.P.2
Shannon, M.L.3
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13
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34848818304
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For the synthesis of an allylic amine via a silaaziridine intermediate, see
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For the synthesis of an allylic amine via a silaaziridine intermediate, see: Nevárez, Z.; Woerpel, K. A. Org. Lett. 2007, 9, 3773-3776.
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(b) Franz, A. K.; Woerpel, K. A. Angew. Chem., Int. Ed. 2000, 39, 4295-4299.
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Franz, A.K.1
Woerpel, K.A.2
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16
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62149107941
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All of the insertion products shown in Tables 1 and 2 were isolated and purified by a hexane extraction from an acetonitrile solution of the reaction mixture in an inert atmosphere glovebox. This procedure allowed the products to be separated from the copper catalyst and avoided hydrolysis of the Si-N bonds of these sensitive products. Additional confirmation of structure was obtained for the corresponding hydrolysis products; details are provided as Supporting Information.
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All of the insertion products shown in Tables 1 and 2 were isolated and purified by a hexane extraction from an acetonitrile solution of the reaction mixture in an inert atmosphere glovebox. This procedure allowed the products to be separated from the copper catalyst and avoided hydrolysis of the Si-N bonds of these sensitive products. Additional confirmation of structure was obtained for the corresponding hydrolysis products; details are provided as Supporting Information.
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17
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62149115721
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1H NOESY experiments.
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1H NOESY experiments.
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18
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62149127079
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For transition-metal-mediated reductive coupling reactions of alkynes and imines, see: (a) Reference 1d.
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For transition-metal-mediated reductive coupling reactions of alkynes and imines, see: (a) Reference 1d.
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19
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34447529183
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(b) Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432-8433.
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Barchuk, A.1
Ngai, M.-Y.2
Krische, M.J.3
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20
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62149128245
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Reference 1g
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Reference 1g.
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21
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62149116083
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Details are provided as Supporting Information
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Details are provided as Supporting Information.
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22
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36048951463
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For recent examples of reductive amination under acidic conditions, see: a
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For recent examples of reductive amination under acidic conditions, see: (a) Reddy, P. S.; Kanjilal, S.; Sunitha, S.; Prasad, R. B. N. Tetrahedron Lett. 2007, 48, 8807-8810.
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Tetrahedron Lett
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Reddy, P.S.1
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(b) Heydari, A.; Arefi, A.; Esfandyari, M. J. Mol. Catal. A: Chem. 2007, 274, 169-172.
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Heydari, A.1
Arefi, A.2
Esfandyari, M.3
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24
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62149150343
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3N or using silanized silica gel or alumina did not improve the purification.
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3N or using silanized silica gel or alumina did not improve the purification.
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25
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37049109987
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For examples of additions of enamines to acrylonitrile and methyl acrylate, see: (a) de Jeso, B, Pommier, J.-C. J. Chem. Soc, Chem. Commun. 1977, 565-566
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For examples of additions of enamines to acrylonitrile and methyl acrylate, see: (a) de Jeso, B.; Pommier, J.-C. J. Chem. Soc., Chem. Commun. 1977, 565-566.
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28
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(d) Fourtinon, M.; de Jeso, B.; Pommier, J.-C. J. Organomet. Chem. 1985, 289, 239-246.
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Fourtinon, M.1
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Pommier, J.-C.3
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6444221257
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For examples of enamine hydroboration, see: (a) Butler, D. N, Soloway, A. H. J. Am. Chem. Soc. 1966, 88, 484-487
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For examples of enamine hydroboration, see: (a) Butler, D. N.; Soloway, A. H. J. Am. Chem. Soc. 1966, 88, 484-487.
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30
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(b) Goralski, C. T.; Hasha, D. L.; Nicholson, L. W.; Zakett, D.; Fisher, G. B.; Singaram, B. Tetrahedron Lett. 1994, 35, 3251-3254.
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Goralski, C.T.1
Hasha, D.L.2
Nicholson, L.W.3
Zakett, D.4
Fisher, G.B.5
Singaram, B.6
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The allylic amino alcohol was isolated in 85% yield with >90% purity. This compound was of sufficient purity to be used in subsequent reactions. Purification by chromatography provided a 44% yield of the allylic amino alcohol.
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The allylic amino alcohol was isolated in 85% yield with >90% purity. This compound was of sufficient purity to be used in subsequent reactions. Purification by chromatography provided a 44% yield of the allylic amino alcohol.
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