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Mitchinson, A.1
Nadin, A.2
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For recent reviews on the stereoselective synthesis of piperidines, see: (a) Laschat, S.; Dickerner, T. Synthesis 2000, 1781. (b) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. For selected recent examples, see: (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (d) Charette, A. B.; Grenon, M. Lemire, A.; Pourashraf M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830. (e) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477-12487.
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For recent reviews on the stereoselective synthesis of piperidines, see: (a) Laschat, S.; Dickerner, T. Synthesis 2000, 1781. (b) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. For selected recent examples, see: (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (d) Charette, A. B.; Grenon, M. Lemire, A.; Pourashraf M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830. (e) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477-12487.
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Grenon, M.2
Lemire, A.3
Pourashraf, M.4
Martel, J.5
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For recent reviews on the stereoselective synthesis of piperidines, see: (a) Laschat, S.; Dickerner, T. Synthesis 2000, 1781. (b) Mitchinson, A.; Nadin, A. J. Chem. Soc., Perkin Trans. 1 2000, 2862-2892. For selected recent examples, see: (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004-1005. (d) Charette, A. B.; Grenon, M. Lemire, A.; Pourashraf M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830. (e) Shu, C.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477-12487.
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Daub, G. W.; Heerding, D. A.; Overman, L. E. Tetrahedron 1988, 44, 3919-3930. Depending on the way iminium ions were generated, partial racemization was also observed.
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85047672030
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For the preparation of α-substituted-crotylsilanes, see: (a) Sparks, M. A.; Panek J. S. J. Org. Chem. 1991, 56, 3431-3438. (b) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003-1010.
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Sparks, M.A.1
Panek, J.S.2
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0000397735
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For the preparation of α-substituted-crotylsilanes, see: (a) Sparks, M. A.; Panek J. S. J. Org. Chem. 1991, 56, 3431-3438. (b) Panek, J. S.; Yang, M.; Solomon, J. S. J. Org. Chem. 1993, 58, 1003-1010.
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Panek, J.S.1
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Solomon, J.S.3
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16
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0012673628
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note
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2, rt, 0.5 h).
-
-
-
-
17
-
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0012736289
-
-
note
-
2O either gave low conversion or were less general in terms of aldehydes employed.
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-
-
-
19
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0012673629
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note
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Enantiomeric excess (ee) analysis was conducted by chiral HPLC analysis. The detailed experimental procedure including ee analysis can be found in the Supporting Information.
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-
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20
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11144349848
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Pelletier, S. W., Ed.; Pergamon: New York. Chapter 1
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Daly, J. W.; Garraffo, H. M.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: New York, 1999; Vol. 13. Chapter 1, pp 1-161.
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Daly, J.W.1
Garraffo, H.M.2
Spande, T.F.3
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21
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0027297056
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(a) Garrafo, H. M. Caceres, J.; Daly, J. W.; Spande, T. F.; Andriamaharavo, N. R.; Andriantsiferana, M. J. Nat. Prod. 1993, 56, 1016-1038.
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Andriantsiferana, M.6
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22
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0030460692
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(b) Jain, P.; Garrafo, H. M. Yeh, H. J. C.; Spande, T. F.; Daly, J. W.; Andriamaharavo, N. R.; Andriantsiferana, M. J. Nat. Prod. 1996, 59, 1174-1178. The absolute configuration and optical rotation of 217A are unknown.
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Jain, P.1
Garrafo, H.M.2
Yeh, H.J.C.3
Spande, T.F.4
Daly, J.W.5
Andriamaharavo, N.R.6
Andriantsiferana, M.7
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24
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0001539666
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(a) Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-5570.
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0001539666
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26
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0012632214
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-
note
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See Supporting Information for details.
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