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Although double reductive amination strategies have been reported, the triple reductive amination approach is not known; see: (a) Reference 5. (b) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (c) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
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Although double reductive amination strategies have been reported, the triple reductive amination approach is not known; see: (a) Reference 5. (b) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (c) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
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Baxter, E.W.1
Reitz, A.B.2
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Although double reductive amination strategies have been reported, the triple reductive amination approach is not known; see: (a) Reference 5. (b) Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175. (c) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
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Martin, O.R.1
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A conceptually similar strategy to the pyrrolidizidine alkaloids involving a double reductive amination-lactam formation sequence has recently been described: Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574.
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(c) Shan, W.; Wilson, P.; Liang, W.; Mootoo, D. R. J. Org. Chem. 1994, 59, 7986.
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1H NMR of both epimers with those of related chain extended gluco derivatives: Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650.
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16044374420
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Availabe from Tocris Cookson, Inc., St. Louis, MO 63146
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Availabe from Tocris Cookson, Inc., St. Louis, MO 63146.
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24
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16044362999
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note
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The related double reductive cyclization on 5-ketoglucose derivatives has also been shown to proceed with high stereoselectivity for the 2,5-imino-D-glucitol: see refs 5 and 8.
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25
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