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Stereoselective Addition of Nucleophiles to Aziridinyl-2-carboxaldimine

  • Kim, Sang-Woo (Department of Chemistry, Hankuk University of Foreign Studies, Center for Bioactive Molecular Hybrids, Yonsei University) ;
  • Noh, Heui-Yoon (Department of Chemistry, Hankuk University of Foreign Studies, Center for Bioactive Molecular Hybrids, Yonsei University) ;
  • Paek, Seong-In (Department of Chemistry, Hankuk University of Foreign Studies) ;
  • Ha, Hyun-Joon (Department of Chemistry, Hankuk University of Foreign Studies, Center for Bioactive Molecular Hybrids, Yonsei University) ;
  • Lee, Won-Koo (Department of Chemistry, Sogang University)
  • Published : 2004.11.20

Abstract

Keywords

References

  1. Lee, W.-K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57.
  2. Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247. https://doi.org/10.1039/b006015l
  3. Zwanenburg, B.; ten Holte, P. In Stereoselective Heterocyclic Chemistry III; Metz, P., Ed.; Springer: Berlin, 2001, pp 93-124.
  4. McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
  5. Osborn, H. M. I.; Sweeney, J. B.; Tetrahedron: Asymmetry 1997, 8, 1693. https://doi.org/10.1016/S0957-4166(97)00177-8
  6. Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Pergamon Press: New York, 1996; Vol. 1A, p 1.
  7. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. https://doi.org/10.1002/anie.199405991
  8. Suh, M.-J, ; Kim, S. W.; Beak, S. I.; Ha, H.-J.; Lee, W.-K. Synlett 2004, 489.
  9. Kobayashi, S.; Ishitani, H.; Ueno, M. Synlett 1997, 115.
  10. Meyer, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656. https://doi.org/10.1021/ja9624073
  11. Li, B.-F.; Yuan, K.; Zhang, M.-J.; Wu, H.; Dai, L.-X.; Wang, Q. R.; Hou, X.-L. J. Org. Chem. 2003, 68, 6264. https://doi.org/10.1021/jo034477f
  12. Sin, T. B.; Kang, S. H.; Lee, K. S.; Lee, W. K.; Yun, H.; Dong, Y.; Ha, H.-J. J. Org. Chem. 2003, 68, 104-108. https://doi.org/10.1021/jo0261911
  13. Park, C. S.; Kim, M. S.; Lee, W. K.; Ha, H.-J. J. Org. Chem. 2003, 68, 43. https://doi.org/10.1021/jo025545l
  14. Akiyama, T.; Itoh, J.; Fuchibe, K. Synlett 2004, 489.
  15. Wenzel, A. G.; Jabobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964. https://doi.org/10.1021/ja028353g
  16. Shimizu, M.; Itohara, S.; Hase, E.; Chem. Commun. 2001, 2318.
  17. Waldman, H. Angew. Chem., Int. Ed. Engl. 1998, 27, 274. https://doi.org/10.1002/anie.198802741
  18. Bromidge, S.; Wilson, P. C.; Whiting, A. Tetrahdron Lett. 1998 39, 8905 https://doi.org/10.1016/S0040-4039(98)01947-9
  19. Ishimara, K.; Kjima, T. J. Org. Chem. 2000, 65, 8395. https://doi.org/10.1021/jo0011888
  20. Yuan, Y.; Ding, K. Org. Lett. 2002, 4, 3309. https://doi.org/10.1021/ol0265822
  21. Ha, H.-J.; Choi, C.-J.; Ahn, Y.-G.; Yoon, H.; Dong, Y.; Lee, W. K. J. Org. Chem. 2000, 65, 8384 https://doi.org/10.1021/jo001109s
  22. Shimizu, M.; Suzuki, I.; Makino, H. Synlett 2003, 1635.
  23. Bhattarai, K.; Cainelli, G.; Panunzio, M. Synlett 1990, 229.
  24. Jacob, P.; Callery, P. S.; Shulgin, A. T.; Castagnoli, N. J. Org. Chem. 1976, 41, 3627. https://doi.org/10.1021/jo00884a035
  25. Dong, Y.; Yun, H.; Park, C. S.; Lee, W.-K.; Ha, H.-J. Acta Crystal. C 2003, 59, 659. https://doi.org/10.1107/S0108270103022698

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