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3-Oxo-2-(triphenyl-λ5-phosphanylidene)-4-(phenylsulfinyl)butanenitrile:An Efficient Reagent for α-Keto (Cyanomethylene)triphenylphosphoranesfrom Alkyl Bromides

  • Published : 2009.11.20

Abstract

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References

  1. Tanaka, H.; Kuroda, A.; Marusawa, H.; Hatanaka, H.; Kino, T.; Koto, T.; Hashimoto, M.; Taga, T. J. Am. Chem. Soc. 1987, 109, 5031. https://doi.org/10.1021/ja00250a050
  2. Fusetani, N.; Matsunaga, S.; Matsumoto, H.; Takebayashi, Y. J. Am. Chem. Soc. 1990, 112, 7053. https://doi.org/10.1021/jm00044a013
  3. Schmidt, H.; Weinbrenner, S. J. Chem. Soc., Chem. Commun. 1994, 1003. https://doi.org/10.1021/cr950025u
  4. Bokesch, H. R.; Pannell, L. K.; McKee, T. C.; Boyd, M. R. Tetrahedron Lett. 2000, 41, 6305. https://doi.org/10.1021/jo00095a005
  5. Harbeson, S. L.; Abelleria, S. M.; Akiyama, A.; Barrett, R.; Carroll, R. M.; Straub, J. A.; Tkacz, J. N.; Wu, C.; Mosso, G. F. J. Med. Chem. 1994, 37, 2918. https://doi.org/10.1021/jo980860m
  6. Harvey, A. J.; Abell, A. D. Tetrahedron 2000, 56, 9763. https://doi.org/10.5012/bkcs.2007.28.10.1641
  7. Kokotos, G.; Kotsovolou, S.; Constantinou-Kokotou, V.; Beltzner, C. C.; Dennis, E. A. J. Med. Chem. 2002, 45, 2891. https://doi.org/10.1021/ja00801a058
  8. Mehdi, S. Biorg. Chem. 1993, 21, 249. https://doi.org/10.1021/cr950025u
  9. Otto, H. H.; Schirmeister, T. Chem. Rev. 1997, 97, 133. https://doi.org/10.1021/cr950025u
  10. Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359 https://doi.org/10.1021/ja01569a043
  11. Wasserman, H. H.; Ho, W.-B. J. Org. Chem. 1994, 59, 4364 https://doi.org/10.1021/jo00095a005
  12. Wasserman, H. H.; Petersen, A. K. J. Org. Chem. 1997, 38, 953. https://doi.org/10.1016/S0040-4039(00)02280-2
  13. Wasserman, H. H.; Wang, J. J. Org. Chem. 1998, 63, 5581. https://doi.org/10.1021/jo980860m
  14. Lee, K. Bull. Korean Chem. Soc. 2002, 23, 351. https://doi.org/10.5012/bkcs.2002.23.2.351
  15. Han, W.; Hu, Z.; Jiang, X.; Wasserman, Z. R.; Decicco, C. R. Bioorg. Med. Chem. Lett. 2003, 13, 1111. https://doi.org/10.1016/S0960-894X(03)00031-3
  16. Lee, K.; Kim, D.-K. J. Korean Chem. Soc. 2004, 48, 161. https://doi.org/10.5012/jkcs.2004.48.2.161
  17. Price, W. S.; Fletcher, S.; Jorgensen, M. R.; Miller, A. D. Synlett 2006, 1933
  18. Lee, K. Bull. Korean Chem. Soc. 2007, 28, 1641 https://doi.org/10.5012/bkcs.2007.28.10.1641
  19. Trost, B. M.; Salzmann, T. N. J. Am. Chem. Soc. 1973, 95, 6840. https://doi.org/10.1021/ja00801a058
  20. Herrmann, J. L.; Berger, M. H.; Schlessinger, R. H. J. Am. Chem. Soc. 1973, 95, 7923.
  21. Trost, B. M.; Leung, K. K. Tetrahedron Lett. 1975, 4197
  22. Bruice, T. C.; Markiw, R. T. J. Am. Chem. Soc. 1957, 79, 3150 https://doi.org/10.1021/ja01569a043
  23. Lee, K.; Im, J.-M. Tetrahedron Lett. 2001, 42, 1539 https://doi.org/10.1016/S0040-4039(00)02280-2

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