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Synthesis of N-Benzyl 3,5-Disubstituted Piperidines via Double Michael Addition Strategy

  • Lee, Mi-Jung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2005.03.20

Abstract

Keywords

References

  1. Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85 https://doi.org/10.1016/S0040-4039(00)01886-4
  2. Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S.; Reddy, R. M. Tetrahedron 2001, 57, 8167 https://doi.org/10.1016/S0040-4020(01)00786-4
  3. Basavaiah, D.; Sharada, D. S.; Kumaragurubaran, N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135 https://doi.org/10.1021/jo0257952
  4. Grigg, R.; Dorrity, M. J.; Heaney, F.; Malone, J. F.; Rajviroongit, S.; Sridharan, V.; Surendrakumar, S. Tetrahedron 1991, 47, 8297 https://doi.org/10.1016/S0040-4020(01)91022-1
  5. Grigg, R.; Malone, J. F.; Dorrity, M. R. J.; Heaney, F.; Rajviroongit, S.; Sridharan, V.; Surendrakumar, S. Tetrahedron Lett. 1988, 29, 4323 https://doi.org/10.1016/S0040-4039(00)80487-6
  6. Hughes, F. Jr.; Grossman, R. B. Org. Lett. 2001, 3, 2911 https://doi.org/10.1021/ol016395o
  7. Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron Lett. 1987, 28, 6675 https://doi.org/10.1016/S0040-4039(00)96943-0
  8. Perlmutter, P.; Tabone, M. Tetrahedron Lett. 1988, 29, 949 https://doi.org/10.1016/S0040-4039(00)82490-9
  9. Hadimani, S. B.; Padmakumar, R.; Bhat, S. V. Synth. Commun. 1996, 26, 3527 https://doi.org/10.1080/00397919608003761
  10. Azizi, N.; Saidi, M. R. Tetrahedron 2004, 60, 383 https://doi.org/10.1016/j.tet.2003.11.012
  11. Correc, O.; Guillou, K.; Hamelin, J.; Paquin, L.; Texier-Boullet, F.; Toupet, L. Tetrahedron Lett. 2004, 45, 391 https://doi.org/10.1016/j.tetlet.2003.10.148
  12. Christoffers, J. J. Chem. Soc., Perkin Trans. 1 1997, 3141
  13. Elbein, A. D.; Molyneux, R. In Alkaloids; Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, 1987; Vol. 57, P. 1
  14. Collins, I.; Davey, W. B.; Rowley, M.; Quirk, K.; Bromidge, F. A.; McKernan, R. M.; Thompson, S.-A.; Wafford, K. A. Bioorg. Med. Chem. Lett. 2000,10, 1381 https://doi.org/10.1016/S0960-894X(00)00245-6
  15. Kim, B. M.; Shaw, A. W.; Graham, S. L.; Desolms, S. J.; Ciccarone, T. M. US 5817678A, 1996
  16. Park, J.-S.; Yeom, C.-E.; Choi, S. H.; Ahn, Y. S.; Ro, S.; Jeon, Y. H.; Shin, D.-K.; Kim, B. M. Tetrahedron Lett. 2003, 44, 1611 https://doi.org/10.1016/S0040-4039(03)00002-9
  17. Liang, X.; Lohse, A.; Bols, M. J. Org. Chem. 2000, 65, 7432 https://doi.org/10.1021/jo000699r
  18. Danieli, B.; Lesma, G.; Passarella, D.; Silvani, A. Tetrahedron: Asymmetry 1996, 7, 345 https://doi.org/10.1016/0957-4166(96)00002-X
  19. Danieli, B.; Lesma, G.; Passarella, D.; Silvani, A. J. Org. Chem. 1998, 63, 3492 https://doi.org/10.1021/jo972067j
  20. Iding, H.; Wirz, B.; Sarmiento, R.-M. R. Tetrahedron: Asymmetry 2003, 14, 1541 https://doi.org/10.1016/S0957-4166(03)00283-0
  21. Igarashi, J.; Ishiwata, H.; Kobayashi, Y. Tetrahedron Lett. 2004, 45, 8065 https://doi.org/10.1016/j.tetlet.2004.08.174
  22. Pave, G.; Leger, J.-M.; Jarry, C.; Viaud-Massuard, M.-C.; Guillaumet, G. J. Org. Chem. 2003, 68, 1401 https://doi.org/10.1021/jo026228h
  23. Roa, L. F.; Gnecco, D.; Galindo, A.; Teran, J. L.; Bernes, S. Tetrahedron: Asymmetry 2004, 15, 847 https://doi.org/10.1016/j.tetasy.2004.01.017
  24. Concellon, J. M.; Riego, E.; Rivero, I. A.; Ochoa, A. J. Org. Chem. 2004, 69, 6244 https://doi.org/10.1021/jo0490806
  25. Danieli, B.; Lesma, G.; Passarella, D.; Piacenti, P.; Sacchetti, A.; Silvani, A.; Virdis, A. Tetrahedron Lett. 2002, 43, 7155 https://doi.org/10.1016/S0040-4039(02)01671-4
  26. Cook, C. E.; Wani, M. C.; Jump, J. M.; Lee, Y.-W.; Fail, P. A.; Anderson, S. A.; Gu, Y.-Q.; Petrow, V. J. Med. Chem. 1995, 38, 753 https://doi.org/10.1021/jm00005a003
  27. Meyer, M. D.; DeBernardis, J. F.; Hancock, A. A. J. Med. Chem. 1994, 37, 105 https://doi.org/10.1021/jm00027a013
  28. Booth, R. G.; Trevor, A.; Singer, T. P.; Castagnoli, N. Jr. J. Med. Chem. 1989, 32, 473 https://doi.org/10.1021/jm00122a031
  29. Murthy, K. S. K.; Rey, A. W.; Tjepkema, M. Tetrahedron Lett. 2003, 44, 5355 https://doi.org/10.1016/S0040-4039(03)01192-4
  30. Clarke, R. L.; Gambino, A. J.; Daum, S. J. J. Med. Chem. 1974, 17, 1040 https://doi.org/10.1021/jm00256a002
  31. Montoro, R.; Marquez, F.; Llebaria, A.; Delgado, A. Eur. J. Org. Chem. 2003, 217
  32. Hill, R. K.; Chan, T.-H. Tetrahedron 1965, 21, 2015 https://doi.org/10.1016/S0040-4020(01)98340-1

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