Palladium-catalyzed rearrangement of allylic sulfoximines: Application to the asymmetric synthesis of chiral allylic amines

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5517-5522

  Pyne, Stephen G ^a   Dong, Zemin ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000324618     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9605105     Document Type: Article

References (27)

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2. For some recent examples, see: (a) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (b) Davies, S. G.; McCarthy, T. D. Synlett 1995, 700. (c) Matulenko, M. A.; Meyers, A. I. J. Org. Chem. 1996, 61, 573. (d) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424.
3. For some recent examples, see: (a) Nishibayashi, Y.; Arikawa, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 1996, 61, 1172. (b) Davies, S. G.; McCarthy, T. D. Synlett 1995, 700. (c) Matulenko, M. A.; Meyers, A. I. J. Org. Chem. 1996, 61, 573. (d) Miao, G.; Rossiter, B. E. J. Org. Chem. 1995, 60, 8424.
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22. For the [2,3]-sigmatropic rearrangements of allylic selenilimines, sulfilimines, and tellurimides, see refs a, b, and c, respectively: (a) Frankhauser, J. E.; Peevey, R. M.; Hopkins, P. B. Tetrahedron Lett. 1984, 25, 15. (b) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137. (c) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725. (d) For more recent references, see: Dolle, R. E.; Li, C.-S.; Novelli, R.; Kruse, L. I.; Eggleston, D. J. Org. Chem, 1992, 57, 128. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc. Chem. Commun. 1995, 1243 and references cited therein.
23. For the [2,3]-sigmatropic rearrangements of allylic selenilimines, sulfilimines, and tellurimides, see refs a, b, and c, respectively: (a) Frankhauser, J. E.; Peevey, R. M.; Hopkins, P. B. Tetrahedron Lett. 1984, 25, 15. (b) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137. (c) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725. (d) For more recent references, see: Dolle, R. E.; Li, C.-S.; Novelli, R.; Kruse, L. I.; Eggleston, D. J. Org. Chem, 1992, 57, 128. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc. Chem. Commun. 1995, 1243 and references cited therein.
24. For the [2,3]-sigmatropic rearrangements of allylic selenilimines, sulfilimines, and tellurimides, see refs a, b, and c, respectively: (a) Frankhauser, J. E.; Peevey, R. M.; Hopkins, P. B. Tetrahedron Lett. 1984, 25, 15. (b) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137. (c) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725. (d) For more recent references, see: Dolle, R. E.; Li, C.-S.; Novelli, R.; Kruse, L. I.; Eggleston, D. J. Org. Chem, 1992, 57, 128. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc. Chem. Commun. 1995, 1243 and references cited therein.
25. For the [2,3]-sigmatropic rearrangements of allylic selenilimines, sulfilimines, and tellurimides, see refs a, b, and c, respectively: (a) Frankhauser, J. E.; Peevey, R. M.; Hopkins, P. B. Tetrahedron Lett. 1984, 25, 15. (b) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137. (c) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725. (d) For more recent references, see: Dolle, R. E.; Li, C.-S.; Novelli, R.; Kruse, L. I.; Eggleston, D. J. Org. Chem, 1992, 57, 128. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc. Chem. Commun. 1995, 1243 and references cited therein.
26. For the [2,3]-sigmatropic rearrangements of allylic selenilimines, sulfilimines, and tellurimides, see refs a, b, and c, respectively: (a) Frankhauser, J. E.; Peevey, R. M.; Hopkins, P. B. Tetrahedron Lett. 1984, 25, 15. (b) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137. (c) Nishibayashi, Y.; Srivastava, S. K.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1995, 36, 6725. (d) For more recent references, see: Dolle, R. E.; Li, C.-S.; Novelli, R.; Kruse, L. I.; Eggleston, D. J. Org. Chem, 1992, 57, 128. Nishibayashi, Y.; Chiba, T.; Ohe, K.; Uemura, S. J. Chem. Soc. Chem. Commun. 1995, 1243 and references cited therein.
27. Pyne, S. G.; Dong, Z.; Skelton, B. W.; White, A. H. J. Chem. Soc., Perkin Trans. 1 1994, 2607.